Art by Sam Liacos.
Illustration by Sam Liacos.

Friend with Benefits is ILY’s biweekly advice column, spearheaded by Rae Witte. If you’d like to submit a question, email her at or tweet her your question at @raewitte using the hashtag #askily.

Entry 39: January 24, 2020

Is it ever the right time to approach a woman as the other woman? 

My gut instinct is no. I met someone in September and casually invited him to a sporting event because I had extra tickets. We hit it off and realized at the end of the night we had a lot in common and similar lifestyle choices. He asked me on a date and we confirmed that we were interested/attracted to each other. He started to back off in the following week(s) and when I asked him what was good, he professed he was dating someone else who lived thousands of miles away.

A few weeks went by and we ran into each other, and he texted me the next day saying how nice it was to see me and we made plans. We hung out twice that weekend and finally had sex. A few days after I went on a hunt to find out who the person he was dating was (he was really good at not posting on social media). They were much more than casual dating—it was clear she was in love with him. Months later, he’s still taking me on dates, gifting small but meaningful items, and has never opened up about his situation. We’ve both agreed about our strong connection and comfortability with each other, but I know it most likely won’t go anywhere because of her. 

Is it right for me to ask [for] details? I assume they may be in an open relationship due to distance (they’ve been together a year) or that they’re not in a full relationship. I don’t think it’s worth it to approach the other woman, but I have a feeling she doesn’t know what’s up. 

I think at some point I should run—the very way I met him.

While I’m not here to fully diminish the potential of a “woman to woman” conversation, this is absolutely not the circumstance for that convo for multiple reasons. Your gut is right. First and foremost, I don’t really know what you’d (or anyone) gain from you contacting her when you’ve been knowingly carrying on with her man. 

I am a little concerned about the way you’ve worded your view on the situation. Just because she posts all over her social media about him and he doesn’t, doesn’t mean he doesn’t have her under the impression that he too is in love with her. Also, if the difference is so stark, it’s fair to assume she knows he’s not posting her. Any ideas you have about their relationship beyond that, is you taking the plunge into a sea of your own conclusions, rather than just asking him.

Further, if you feel like it most likely won’t go anywhere, it’s not “because of her.” It’s because of him and his secrecy around her, what he’s doing with you, and the reality that you don’t know if you trust him. 

Also, throughout your entire question, you didn’t mention what you want and what you are okay with, but you did discuss what you think you need to do with circumstances that you aren’t even really clear about. It’s time to stop speculating on your own. 

Her not knowing what’s up isn’t your problem, but it’s not not your business, if that makes sense. You don’t need to inform her what her man is doing, because you don’t know what their relationship is. However, because you are dating him, it is your business to have a discussion on where you and he stand, what you want or don’t want, and are comfortable or uncomfortable with happening outside of your relationship. 

I think the two things you should do are dependent on what it is you want and are okay with and how to approach him about it. If you are going to move forward without a discussion with him, do that and don’t hit her up. Figure out how it is you want this relationship to exist in your life (if at all), and then put in the steps to make that happen with the person you’re in the relationship with. 

If you’ve established you have a strong connection and comfortability, it’s time to put it to the test and have some uncomfortable conversations that have the potential to strengthen or break the bond.

Entry 38: January 10, 2020

Over the last six weeks or so, three women have been making pretty overt advances towards me despite me telling them that I’m seeing someone and that I’d like them to stop. I’ve never had a sexual encounter with any of them, though I’ll admit to polite flirtation and casual conversation in which we talked about sex—their love life or mine, but not about the possibility of us together. 

One, a freelancer who I’ve worked with for a while but have never been in the same room with, sent unsolicited nudes twice. The second time she did, it actually came after I told her I couldn’t work with her if she did it again. Apparently that didn’t phase her. Two others, including another writer and a woman in PR I’ve worked with, have called after midnight asking that I come over and called again when I said “no,” either to demand I explain why I won’t fuck them or to challenge my masculinity. The volume of these seemed to only go up when I told them I was seeing someone. I had mentioned in passing that we weren’t exclusive yet, and this seemed to leave the door open. I woke to another 1 a.m. missed call this morning, which is why I’m sending this email. 

Obviously, this is something women deal with daily, and no one feels bad for the white guy who’s regularly getting offered sex. But I think that leads to me not being taken seriously when I tell someone to stop, and I also don’t feel like I can talk or post publicly about it without the ridicule being reflected back on me, again challenging my masculinity or just flatly telling me to “shut the fuck up.” It’s especially weird that all these stem from work relationships. In the past, I might have given in to the offers (I’m very attracted to one of these women), but I’m really into the woman I’m seeing and not trying to fuck that up. 

So what do you think? What’s my recourse for this kind of thing? How can guys be taken seriously when a woman who has a paycheck threatened can roll her eyes and just do it again? Why do these women think it’s OK to continue to call or text or send pictures when they’d likely find it appalling if someone else was doing the same to them? Or am I being naive?

First of all, I don’t think you’re being naive. This is textbook sexual harassment (unwelcome and inappropriate sexual remarks or physical advances.) However, I’m not surprised at the discomfort of addressing it or it escalating, since the conversation around sexual harassment we mostly hear about largely focuses on when the genders are reversed, and even then, the one being harassed often struggles with how to handle it. 

While I think it’s very understandable you’d think no one feels bad for an established white dude getting offered sex aggressively, it’s this very idea that’s left you (and probably other men) without the tools to address it. Further, the gender dynamics of women being socialized to treat sex as something they give to men or that has to be earned by men rather than something for their pleasure also probably plays into why your rejections are met with demands for why or attacks on your masculinity, because the stereotype is that men always want sex. None of this patriarchal bullshit makes it okay. No always means no, no matter who says it. 

You mentioned telling the unsolicited nude sender that you wouldn’t commision her work if she continued to send nudes after being asked not to. I think you should follow through. You should tell her she crossed a line and not commission her or work with her for a bit. 

I also think in order to avoid coming off as mansplaining harassment or patronizing like “what would you do if a man you weren’t into was doing this to you” or “if you were in my shoes,” you should set boundaries specific to your relationships with these women and not bring the topic of sexual harassment as a whole into it.  

I’m thinking something along the lines of, “I expressed I’m not interested. It’s really disappointing that you’d call my masculinity into it when no simply means no.” I always try to walk people through what they did, how it made me feel, and how I’d like to proceed. “I said (fill in the blank). When you did (fill in the blank), I felt bad/disrespected/frustrated/etc. Is that your intention? I don’t want to do this again.”

Since they are work relationships, I think the right route is to address that what’s occurred will affect working together, and you should take that with the others, too. A married superior of mine would get drunk and high and text me wildly inappropriate things when I was 19 or 20, but I knew I didn’t want to leave the job. It was only for the summer, and I felt like it would look great on my resume. I told him that I really liked working with the program and pointed out he was married. I said, “I trust you won’t put me in a position again where I have to speak to someone about you continually crossing these lines so we can continue to work together.” Then I had to let it go, but he didn’t. I was surprised, but I feel like he knew he put himself in a position for me to hurt his marriage and career. He was such a creep, and I’m sure there were other women he was propositioning. 

You have to follow through with what you say you’re going to do if they cross those boundaries. If you don’t follow through, they aren’t going to stop. 

Lastly, as for the one woman you are attracted to, maybe I’m wrong, but I get the feeling that you don’t want to shut that down forever, but it definitely needs to be shut down right now. Try something like, “I think really highly of you and want to continue to work together, but provided my relationship, I won’t be (fill in the blank) and appreciate you not (fill in the blank) anymore. If you do continue, I’m going to stop working with you.” It’s disrespectful for her to continually cross the line. 

Good luck.

Entry 37: December 6, 2019

I’ve been talking to this guy for about a year. We’re long distance. Everything is really great. We’re hella compatible in every way. We both want a future together, [the] list goes on. 

We were FaceTiming last week and he told me [a] story about an ex who is an artist (it was relevant to the topic we were on) and at the end he says, “but I’m not gonna tell you who she is, cus I think you follow her.” Mind you, I had NO idea that I did prior to the conversation. So it got me thinking a bit, and I figured it out. (We only have one mutual follower and she is an artist, so I know it’s her. She follows me too.) Out of shock, I said nothing. He then said, “I’m not gonna tell you cus you’re gonna put two and two together.” 

He likes all her posts. She is also in a seemingly committed relationship. Now, I have no problem with him liking pics [and] being supportive. I like my guy friends’ pic [and] it’s absolutely nothing because I only feel attracted to my guy. And I get we can be attracted to many ppl at once. But here’s where I’m uncomfortable: she posted this video of her singing and dancing in a mini skirt and she basically angled the camera in a way that you could practically see up her skirt in a mirror…for GOD knows what and he liked it. She has since deleted it, but no other post has bothered me except that one. I hate so much that it bothers me because I know it probably screams trust issues, BUT I HATE IT. Why? Because I can’t tell if he’s just liking to support or lowkey sending signals!!! I would rather it be a damn stranger than his ex. My biggest fear is that he still might have feelings for her or is still attracted to her? Leaving that window open?  Is it wrong to ask? And if not, how do I go about asking in a mature way? I’m really conflicted because they are seemingly very cool with each other from what I’ve seen.

I haven’t addressed it, I just don’t know how. I thought it through and I do want to discuss especially since he was the one who brought it up. I feel uncomfortable with the secrecy. 

He has been incredibly honest throughout this whole time, so this caught me by complete surprise. It’s my first serious ass relationship and I just want to do things right. How do I go about opening communication and transparency about this without seeming insecure and worried about the past?

Throughout this whole note, it seems like your biggest source of discomfort is the unknown and the way this big, unnecessary secret was presented to you, which is valid. The thing is, if you are both on the same page about building a future together, it’s important you find comfort in bringing up when your partner’s actions affect you. 

I don’t think the “trust issues” or insecurity around that photo stem from him liking it as much as when he deliberately told you something and gave little to no context. 

If you are both on the same page about building a future together, it’s important you find comfort in bringing up when your partner’s actions affect you. 

I honestly had a similar situation come up when my now-boyfriend showed me a meme that featured my former dude. The thing is, there was little discomfort from his end (from what I understand) because I’d already explained the situation and my feelings around this person without naming them, so when he showed me the meme, I just told him, “that’s the dude I told you about.” He laughed, and his response was that a lot of what I said made more sense. That was the end of it.

I think you should just be honest and express how little insecurity you felt in the relationship before he brought up this thing, and then closed the door to communicate about it. 

While this may not be the nicest, I tend to spell out how thoughtless actions can be. I can’t understand why he’d make a “thing” out of it, so I’d tell him I want to understand by saying something like, “You told me I followed your ex who was an artist and wouldn’t tell me who it was. I signed on IG. We have only one person in common, and she’s on artist. I obviously went to her page, because I like her art so much that I already follow her. Your secrecy around something I could very easily figure out made me feel a way/bad. Was your intention to put me in this position and make me feel bad? I don’t really understand what your intention was when you brought it up and then made a big deal out of not telling me.” 

I also think it’s strange that the secrecy stems from him thinking it’s negative that you “put two and two together” when it’s something in his past and something that was so easy to figure out. If you are comfortable with it, it’s okay for you to express you’re more comfortable knowing about each other’s past (obviously not every detail) rather than leaving a bunch of doors closed. It’s okay to share each other’s past dating experiences, specifically ones that inform how you are now in a committed relationship. 

Ultimately, if you express your problem or confusion is with how he brought it up and made it a “big secret” rather than the ex or his likes, it will make it easier to discuss. Plus, it’s easier than saying, “I saw you like this deleted Instagram of your ex that you won’t tell me is your ex. What does it mean?!”

Entry 36: November 14, 2019

My ex and I dated for about seven months before he decided he wasn’t ready to be in a relationship. He lied a few times while we dated as well, so that caused some issues, but those lies aside, things were really good between us. When he broke up with me, I was a bit confused and lost, but handled it in a healthy manner and let it go. I did not chase him at all. Six months later, he’s back and telling me he’s made a huge mistake, realized that he’s in love with me, and wants to prove to me that he’s ready. He wants to try again. Yes, I still have feelings for him. They hadn’t fully gone away yet, but I’m hesitant to trust him again. I know most would say that people don’t change and to leave him alone, but I’m not quite sure what to do. Help, please.

While I’m not really of the breed of people that would say people don’t change, I do see some aggressively waving red flags in this situation. 

Before we tackle what to do, I think it’s important for me to ask why the lying seems to hold such little weight with you. I think that’s the root of everything else that followed in your note. I’d also like you to consider what’s most important to you in a partner. Does the lying contradict your desires?

Let me summarize what I’m taking from your question. Someone you dated for seven months decided that after you had been involved in some type of relationship that he wasn’t ready to be in one despite being in one. Now, you might feel like I’m splitting hairs here, and maybe it’s the way you’ve written the question, but stick with me. 

Despite you not offering details about the break up, I understand you were confused, but ultimately accepted it and went your separate ways. I think it would make sense if you were confused because you were involved with someone for seven months that lied to you. The confusion could be founded on you spending seven months together and him deciding he’s not ready for something he’s been doing and the fact that he lied to you several times. This sounds like you don’t trust him and he’s giving mixed signals. 

While you pointed out the other times you had together were good, let me not sugar coat this: he lied, you caught him, and it’s hard to know when someone is being genuine or not lying after that. This is also why you letting it go when he broke up with you makes sense to me. You were put in a position to question what was real about a relationship you were in. 

I know I personally need to work on forgiveness, but it’s hard for me because I think there’s two reasons people lie to their significant others: they don’t think you’re smart enough to see through it, and/or they don’t want to take responsibility for how their actions affect you or others. Either way you spin it, it’s selfish or disrespectful, and do you really need that pattern back in your life? 

So, while I don’t believe once a liar always a liar is 100% accurate and applicable to every situation, I do believe once someone is comfortable lying to you, they will likely continue to lie to you. Personally, I’d prefer to deal with a brand new person’s bullshit or spend some time solo and bullshit-less, rather than deal with someone who has shown me they don’t respect me, repeatedly. 

Entry 35: Oct. 11, 2019

I got stuck in this cycle of leaving and going back to a toxic relationship. It’s finally over now, but while being caught up in that, I damaged a close friendship of mine by repeatedly choosing to go back to someone that truly never had my best interests at heart, which I know now. Hindsight really is 20/20, I guess. I miss my friend. How do I get my them back in my life?

First and foremost, do not attempt to get your friend back if you are still embedded in the cycle. You will do more damage than good if you start to rebuild your friendship only to reintroduce the same behaviors or relationship that caused it to deteriorate. 

An apology from you to your friend is in order. As I’m sure you’ve learned, whether you were faultlessly victimized or an active contributor to the toxicity of that now-abandoned relationship, this broken friendship is not that relationship, and you will need to take responsibility for how your actions or inaction caused a divide in the friendship. 

It would be helpful to know why your friend decided to separate themselves from you. Did they communicate why or not, and if they did, did you acknowledge it? Some reasons why friends walk away from friends who are caught up in toxic relationships are as simple as not being able to handle what’s going on in your life in addition to what’s happening in their own. Sometimes, when we are caught up in these toxic relationships and cycles of unhealthiness in a relationship, it’s hard to be present in our friendships, especially if we’re comfortable leaning on them.

Also, as an outsider looking into your relationship through the lens you allow them to—whether that’s by you sharing details with them or them physically being around with you—there’s only so much some friends can watch you endure (consciously or subconsciously) before they think you should walk away from the relationship. When you don’t, it can be viewed as not valuing yourself or having the self respect to end treatment that isn’t up to the standards they think you’re worth or they believe you should expect from someone. While they can support you, they can’t make you leave, so this could be another reason why they choose to take space. 

Additionally, as you confide in, ask advice of, or are given the strength to leave through your friendships, every time you went back or every day you stay through communicating unhappiness breaks down the trust between you. Your friend may feel as though you always saying one thing and doing another.

Apologizing for specifics around how you neglected the friendship (or yourself) will show you taking ownership rather than blaming it on your ex. I have a friend that was upset with me in the past for not being there for her through her divorce after telling me that she knew she shouldn’t have married him, but she did it for everyone else. Arguably insensitive on my part, I told her I was the friend you tell those things before the wedding, particularly as the only unmarried friend. Months later, she reached out to me saying she realized how it was her lack of ability to speak up or take responsibility for her actions that landed her there, and it was unfair for her to expect everyone to be there not only through the extravagant wedding, but through the nearly immediate divorce. 

I think it’s important to point out that you recognize the value in the friendship and be prepared to hear maybe not-so-nice things about yourself as you discuss what happened in the past and how you’d like to fix it in the future. 

Moving forward together will definitely require rebuilding trust between you, but I think the best thing you can do to initiate that is work on the relationship with yourself. Don’t look to fill the void of the toxic relationship. Getting back to being in a healthy place yourself will make it easier to mend the broken friendship.

Entry 34: Sept. 10, 2019

I met my best friend 5 years ago on a trip abroad. We were both from the same state, but met in another country. We bonded so strongly in a short amount of time that it seemed as though our lives were fated to collide. When we first met, I had the biggest crush on him, but that soon turned into a deep friendship kind of love. At the time, he was in a committed relationship and I had just gotten out of one. We would talk about anything and everything, but most notably our love lives and what we ultimately wanted out of a life partner/lover. I always saw him as a gem in this never-ending sea of men with ill intentions and wanted my future partner to be like him. I never really thought of him actually being the one for me though – call it naïveté or the fact that a year after meeting him i fell in “like” with another guy. When that relationship ended, and I was a new college grad navigating the scary job market, we would meet up for dinner and have these long talks that were healing for me. 

Fast forward to today, we are both single by what seems like some sort of divine intervention, and I can’t help but notice how my feelings for him have shifted from platonic to romantic. I’m unsure if the feeling is mutual however, as we’ve never spoken about us in that way. I’m also worried that things will get awkward if this truth is revealed, but I also think we’re the greatest love story waiting to happen. What should I do? 

I noticed while reading through your entire question that you predominantly spoke about how you view him. You didn’t mention your chemistry or how he treats you outside of what your talks give you – “I never thought of him like that,” “healing for me,” and  “I saw him as a gem.”

It’s important to not let your singleness in this new chapter of your life romanticize your friendship too much, until you really take a look at it in the light and before you make any major moves. I am not saying suppress your feelings, but I am saying altering this relationship does come with a greater risk than the average new guy you date, and taking the next step should be considered at that level. 

While you have this extremely strong bond as friends and the girls he’s dated don’t have that, remove your rose-tinted glasses for a second and remember how he has discussed the women he’s dated and his love life with you. How does he handle rough patches? Conflict? Address his desires? Has he talked about how he valued them? Is he the type to call a woman crazy due to his actions or does he take responsibility for his actions? How he speaks to you, a very close friend, about the women he’s dated could be indicative of how he is in a relationship, even if you guys have a very special friendship. 

Now, I’d like you to take a look at your friendship. Has it always maintained strong when you were seeing other people? And, is it a friendship or does it sit in the murkiness of not being sure if you’ve crossed into flirting?

Finally, now that you’re both single, what do you discuss in terms of your love life? I feel like this would kind of give you some indication of where he’s at. I am in no way suggesting you hide your desire, however, I am saying you should explore these evolving feelings on your own first. 

Once you feel like you’ve taken a step back and become conscious of your exchanges rather than simply your view of him, it could be natural to maintain the normal things you do but maybe take them one step further, kind of like when you’re dating someone new. You don’t just dive into making out (most of the time). So, you said you guys always get dinner, maybe extend the time and get drinks after. Try to be more intentional with your compliments, appreciation and praise of him and the value in your relationship. Flirt a little.

I think running through these questions and putting these feelers out will help you gauge if he is on the same page. Remember to move forward with what feels right for both of you and not just for the story.

Entry 33: August 23, 2019

The long and short is that I asked one of my close friends out a few days after we drunkenly made out. She said she didn’t want a relationship, which I said I respect and we both just agreed to forget about things, but over the month she’s been super nonresponsive/unavailable and I feel like our friendship is deteriorating quite a bit. I’d like to have a real conversation about things, but I know that’s not her style. I’m really concerned about things continuing to fall apart. I’m wondering what, if anything, I should be doing to patch things up.

Before you start to attempt to patch things up, I think it’s important to be honest with yourself. 

Do you have romantic feelings for her?

Throughout your friendship, has it felt like a romantic relationship without the physical intimacy?

Do you simply want a friendship or do you feel more, and are you suppressing those feelings for the friendship?

Obviously, I don’t know the intimate details of your friendship, but in this time of distance between you, it may be a good time to consider the roles in the friendship. Was there a disparity in the emotional labor you each put in? This has a tendency to be a little lopsided in hetero male/female male friendships.

It seems a little extreme she’d let your friendship go purely from a drunken make out and you asking her out. If I put myself in her shoes, the intentional distance may come from her thinking you are actively interested in her intimately. And, since you said she isn’t really one to want to discuss these things, it’s hard to know. 

You mentioned her avoiding you which makes discussing your feelings a little more challenging, especially if she won’t agree to hang out or meet up with you. As much as I hate texting for things like this, it may be best to initiate the conversation there. Starting somewhere like, “Hey, I miss our friendship. I want to apologize for overstepping. Is there anything I’ve done or we can discuss that would make you more comfortable being friends again?” 

I don’t think pretending nothing happened will remedy the situation, but realistically, she does need to meet you somewhere in the middle if you guys are going to mend anything between you. You also do know her and how she handles these intimate situations. I think it’s OK if you send her your thoughts on the situation. For you, I think it’s more about managing expectations. It’ll be very unfortunate if she is unwilling to speak to you about it, but she really might be. It’s important for you to address it with the understanding that you only have so much control over fixing something with someone who doesn’t want to address the obvious distance. 

If she is down to talk, be confident (without being dismissive or sounding arrogant) in communicating what you value about the friendship, that the distance is obvious, and you’d like to fix that. Make her feel safe to tell you why she’s been distant by offering her space to say exactly why she opted to separate herself, without her feeling like she’s going to be told she is wrong. Being distant may not have been the best way to handle her feelings on the situation, but her feelings that led her to do that are valid. 

I think with the time you take to reflect and sort everything for yourself, she’s also had a little time, and with time and showing you are there to listen and want to fix things, you guys will find a way to have your friendship move forward.

Entry 32: July 30, 2019

Trigger warning: The following entry features explicit, potentially distressing language.

OK so to start, some back story … I moved away from California three years ago to Pennsylvania. I have had this girl who has been my right hand since we were in 3rd grade. (I am 24 now.) We were inseparable for years until high school when we kind of split into different friend groups, but our sister dynamic was still very intact. 

We would go weeks even months not talking and then be able to just randomly call each other up or come over to their house and it was like we never left. It was a special thing. We both are very different, and I’ve known it for years. I was the shy one, and she was very outgoing. I struggled with depression which is something we both knew about before I ever tried suicide the first time junior year. She was there just like I was when her parents went through some bad things and her family broke apart. My family took her in always. She was another daughter to them. 

Despite everything, I stayed quiet on things that she did that didn’t rub me right. She had some bad boyfriends who made her do a lot of bad shit, and being in middle school and high school I kind of just ignored it, because that was my ride or die. I let her do her thing, whatever. We grew up separately, and when I moved, it ultimately made me realize I should grow away from her too. 

We tried to keep in contact the first year, but the distance and new environment made my depression worse, and I would stop texting back or answering calls. She gave me a lot of shit for it. I would let her know I was going through it with the move, and she always seemed to throw in my face how she was going through it as well. I was being selfish and not caring about her and the truth was, I know I was. I didn’t want to care about her because I finally got to a point and a literal place where I didn’t have to deal with her sketchy life. 

She got pregnant last year and had a baby this January with a guy I really didn’t like who had her doing all sorts of wild shit. I never said a word about how I really felt to her, because I felt it wasn’t my place since I know she was going through shit and wanted that family vibe in her life. 

Now, I don’t have a desire for kids or marriage. She knows that. And although it may make me look like a shit person, but I didn’t really care for hearing about her pregnancy or anything like that. I talked to my parents, my sister, boyfriend everyone about it, because I felt bad that I didn’t have a desire to ask her about any of it. I ended up telling her this, and she obviously flipped shit. To the point where she told me next time I should try harder next time I try to kill myself. Only one of us seem to have grown up apparently. But this whole thing left me thinking about if I’m a shit person to her, and if I should’ve treated her different and if there is anything else I should do.

Truthfully, it’s kind of a miracle you both maintained a level of friendship this long. I think I have one friend that I am still very close to from my childhood. We’re in our 30s, and that is OK. People in your life will grow differently from you for the rest of your life. Not all childhood friends make it into adulthood (no matter how close you once were), and honestly, not all genuine, substantial friendships you establish as an adult last forever either. However, it doesn’t mean you don’t have a hand in the undoing of a strong bond. 

Friend breakups are just as heartbreaking — if not more — than romantic break ups, because when we enter a romantic relationship, we all know there’s a chance it won’t be forever. You don’t share your deepest secrets, most private thoughts, and hardest laughs over a period of years with someone you don’t anticipate being in it for the long haul. 

For yourself and your future (presumably without her in it), I think it’s important to examine why you stayed quiet on things that didn’t rub you right through middle and high school. There’s a lot of space between letting someone do their thing and mentioning your genuine concern without coming off judgmental. Was it because you had your own stuff? Did you not care about the outcome? What about them rubbed you the wrong way? I don’t think you’re a bad person for not saying anything, but it seems like this was the beginning cracks of the friendship. I think it’s something worth reflecting on without being too hard on yourself or blaming yourself for anything. You were kids. You are more self aware now, and hopefully can learn from it to bring your best self to current and future friendships. 

Where I do think you can take some responsibility for is your aloofness when she was clearly fighting to maintain a relationship with you. I don’t think it’s bad you wanted to lessen the relationship, however, I’m sure it must’ve sucked to feel kind of abandoned by you. 

That said, having communicated your move heightened your depression — and you seemed to be coping through a level of isolation — only to have her attack you for her also struggling at the same time seems like you both lacked the ability to healthily communicate through your struggles and keep the friendship in tact. This alone, makes me understand why you would want to distance yourself from the relationship. 

Obviously, I don’t know the words you used, but I do believe it’s good you were clear about growing apart, the guilt you felt, and ultimately, the lack of desire to keep up with her life. Naturally, this isn’t going to be easy for anyone to hear, but her response is very telling. Like you said, it seems you’ve grown differently, minimally. 

Finally, I feel like her comment about you trying harder to kill yourself is your out of the friendship. Not that you need to have one, but if you feel like clearly communicating you are done with what’s left of the friendship, this is the point of reference. Perhaps saying (or sending) something like, “I know you’ve felt I’ve been absent in a lot of ways you didn’t like, and I probably could’ve communicated better through those times, but your comment on how I should try harder to kill myself crossed a line for me. We’re not friends, and we’re not going to be friends.”

Forming boundaries for yourself isn’t easy, but it does stimulate growth by leaving old habits, old feelings, old places, and even old relationships behind. While I do think there are some ways you could have handled things differently in the past, it seems you’re on the road to communicating your feelings and your needs in friendships. Don’t beat yourself up over your lack of ability to talk through tough things when you were 14. Nothing good will come of that, and it doesn’t define who you are today. 

At this point, I think it’s important to take what you can, will, and won’t do in future friendships, and remember, forever friends are amazing, but the idea that history can be the only thing that maintains some friendships will likely put your own personal growth on hold. 

Entry 31: July 3, 2019

Hi, I need some advice about what to do about women I’m interested in that I work with. I feel like this is something I’ve always had trouble navigating. In my head, I see it going poorly unless there’s already a rapport with the person. I don’t want to be that guy bugging women at work, so I’ve always avoided doing this. I understand if this is too general, but I would appreciate any insight you have to offer. In my current situation, this person longer tenured, a few years my senior and in a different department, but it’s a workplace of about 50 people, so everyone knows everyone to an extent. 

It’s definitely normal to feel as if you’re having trouble navigating it, because it is typically frowned upon by employers, and as you mentioned, you don’t want to be that guy bugging women at work. 

I think the main difference between being that dude and not being that dude is reciprocity. While I’d err on the side of not doing it generally (having done it and it turning out terrible and also good, two separate times), I’d take things significantly slower than you normally would. You see each other everyday, so it isn’t like time isn’t on your side — but if it goes left, you will continue to see each other everyday. 

Another important thing I want to point out is the differences in you at work and you outside work. Expectedly, your work crush may present a little more professionally at work than she would outside of work, which brings me to my next point. Before you really consider making any sort of intimate move, I think the priority should be attempting to get to know this person outside the office first. 

Do you guys chat at work? Flirt on slack? See each other at the water cooler or in the kitchen? Do you ever work together on projects? It would be helpful to know if there is some existing chemistry between you or if this is more of a one-sided crush. 

If there is some sort of rapport established, start small. A walk to get coffee or grabbing lunch together is a great first step in that direction and should come far before asking to grab drinks after work. Small talk about work makes sense, but another easy conversation point that isn’t so obvious about trying to get to know her outside of work is asking plans for the weekend or what she did last weekend. This should be an easy way to find out her interests and see if there’s anything you relate to that you like to do. 

Another quick tip in getting to know anyone, offer them something. If you find out she likes a certain food or activity, offer her a recommendation rather than something like, “Oh, you’ll have to teach me how to do that” or “put me on.” Maybe I’m particular, but I prefer someone participating in the conversation rather than asking me for things. 

I don’t think her longer tenure really matters as long as you don’t cross any lines or do anything inappropriate in the big picture. It may matter to her, but you’ll cross that bridge if you get to it. 

Lastly, do everything in your power not to be that guy at work. If she turns down your advances for the small things (coffee, lunch, a walk, etc.), do not ask for more or bigger things. It’s important to not make things uneasy at work for both of you. If you get to the point where you can express interest and she declines, respect it and let her know you respect it. 

Entry 30: June 7, 2019

Hi Rae,

I’m six months into my new job and things are going very well. Pretty much the entire time since I’ve started, a co-worker and I have engaged in some heavy flirting (not around others, of course). I should also mention I’m in a long-term relationship that I haven’t been quite happy with the last few months (no excuse, though).

A few days ago, after too many happy hour drinks, we finally hooked up, and it was just as amazing as I’ve dreamed it would be. Of course, I feel a lot of guilt about what I did and I am planning on telling my partner once I have a little bit more time to sort out my feelings. This afternoon my co-worker and I had coffee to mull over the details of our night together and decide what to do next. To my surprise (He’s a notorious player. I know. I am the absolute worst), he told me that he doesn’t think it should happen again and that he doesn’t want to get in the middle of my relationship.

This is admirable but really threw me for a loop. He also decided to tell me that even I was single he wouldn’t want to date me, and that he’s been interviewing for other jobs and wants to me. I know it’s what I deserve, but this flat out rejection is hurtful and it makes me realize that my feelings for him are much stronger than I realized.

Right now, I’m looking for advice on how I can salvage our professional relationship. We work closely together in a small marketing team and rely on each other for quite a bit to get the job done. I’m hoping time will help, but is there anything else I can do?


A Confused Lady-Asshole

Oh, dear. Seeing as how this requires some speedy action, the first order of business is acceptance. Despite the typically wretched feeling of outright rejection, acceptance expedites the process of moving forward, and it gives you a pretty clear-cut plan of action. While this is going to be a lot easier said than done, you need to accept the reality of what he’s said to you (regardless of how misleading he was and how sneaky you’ve been) and act accordingly.

This might be just as painful to read as what he has said to you, but here are the facts:

  • You cheated on your partner.
  • You slept with a co-worker — from a close, small team at a good job — that is a “player.”
  • Not only does he not want to “get in the middle” of your relationship (despite already doing exactly that), he says he wouldn’t be interested in dating even if you were single.
  • This hurts and its confusing, and as you’ve said yourself, you’ve brought most of this upon yourself.

Accept these things, take responsibility, remedy them, and move forward.

I am going to be honest, and I very well could be completely wrong, but I think the rejection from the co-worker hurts more because your infidelity doesn’t seem “worth” it any longer seeing you’ve altered an enjoyable relationship at your job, compromised your already waning relationship, and are ultimately going to have to work through these things solo more so than your actual feelings for your co-worker.

I think there’s three things that need to be examined: how you will work together with your co-worker, what you are going to do about your relationship, and how you are going to work on you.

Let’s start with your relationship. Before you come clean to your partner, I think it’s important for you to decide what you want with that relationship. You expressed that it has been on the rocks. This is kind of a crossroads situation for you, and obviously I’m not sure if you have or haven’t done everything in your power to communicate your needs or your feelings of something not being right, but that is one of your options. You need to break it off or decide to put your all into fixing it.

I also don’t know that it is entirely necessary to tell him you cheated, and it’s not because I think you should get away with it. If you are going to break up, this just adds more salt to the wound. Sometimes I think confessing the hurt you’ve done to someone is equally as selfish as doing it. You are getting it off your chest for you, not for them.

If you want to work on your relationship, you need to find the words to say what’s lacking, how you want to contribute to fixing it, and what you need.

If you want to work on your relationship, you need to find the words to say what’s lacking, how you want to contribute to fixing it, and what you need. However, do not stay because you’re feeling rejected by someone else, stay because you want to be with this person. I’m not sure how long the relationship has been unfullfiling, but it seems the flirting and the interest for your co-worker made it clearer. It also sounds like you may not be ready or in a secure enough standing with yourself to put an invested foot forward to fix an unfulfilling relationship that you unfortunately, whether subconsciously or not, may have worsened or officially ended.

If you don’t want to be with them, accept that being single and investing deeply in yourself is the next step. This could be a pivotal time for you to let go of the co-worker and the relationship you’ve been less than satisfied in and reinvest your time into yourself, interests (old and new), friends, and/or new ventures.

Set boundaries for yourself in your communication with him, and shift your focus very deliberately to your work.

As for your co-worker, there isn’t much you can do about his actions, but you are in control of your actions and your feelings. In my unabashedly bias opinion, dudes tend to preach that sex doesn’t have to change things while acting significantly different from before sex. I think communicating you respect and accept his stance on what happened is a good step in making things less weird, but you also have to make sure your actions match those words. Set boundaries for yourself in your communication with him, and shift your focus very deliberately to your work. You don’t need to act like nothing happened, but you do need to accomplish your work. This is going to take a lot of self-discipline and taking accountability for your actions, but from what you wrote to me, it seems you’re self-aware enough to handle this. By prioritizing the work, hopefully you’ll be able to move forward and see some positivity come from this.

While it may feel terrible to have someone outright reject you, in the long run, I think you’ll look back and be grateful there wasn’t some purgatory time frame of wondering what was going on between you and where you stand while at your job.

Lastly, you need to reflect on what got you here, learn what you will and won’t do and how your actions affects others, be better, and charge it to the game.

Entry 29: May 24, 2019

I’ve been with my guy for a year and five months now, and I’m constantly at his place and sleeping over. I was single for four years before him and really got into this routine of really prioritizing my alone time with myself and working out and just being present with myself constantly. When I get into relationships I notice I kind of throw that away and put all attention on the other person. It’s something I notice and want to fix and I try but when I do go home and am alone I feel empty. I don’t like depending on other people like this and really want to get back to focusing on myself more than anything.

It sounds like you feel like you’re neglecting yourself to spend a lot of time with him, but you don’t exactly feel it’s at a detriment to you. This same self-awareness, though, will guide you to make changes and to focus on you. I have to ask, is there anything or anyone else you’re neglecting? Do you still see your friends? Did you spend more time with family before? Are there hobbies or interests that you no longer invest as much (if any) time into because your energy is focused on your relationship and your partner?

Before we get to remedying this, I think it’s important to try to understand why you feel empty when you’re alone. Four years single is nothing to scoff at and has to have offered some sense of security within yourself. I also don’t think you should just be spending time alone just to check a box saying you did. Try to look back at the ways you were present with yourself and all the good that offered you, and try to spend your time alone with intention. Life is different now, so your alone time is not going to look the same as before. You are in a relationship, but it doesn’t mean you have to allow the relationship with yourself to be an afterthought.

I think the best way to get back into being present with yourself and strengthening the relationship with yourself is through routine. Getting back into the habit of working out is always a challenge, but it’s almost always rewarding. That might be a good place to start. Whether it’s going to the gym by yourself or signing up for a class, setting aside a specific time will make it easier to hold yourself accountable. It’s very easy to fall into a habit of just rolling with the punches and going with whatever when you have someone by your side. Putting a few things on your schedule each week can get you more comfortable with your independence again. One workout, one coffee date with a friend, and maybe one other time frame to do something you really care about that’s fallen by the wayside can get you back on track to feeling like there’s a sense of balance, and truthfully, that might be as little as three hours taken from the time you spent together. Totally doable.

Ask for his support or help in holding you accountable for the things you set up for yourself.

Lastly, it seems you are in a relationship with a lot of ease and comfort around each other. Don’t hesitate to communicate your awareness of how you were before versus how you are now and that you’d like to make some changes or find some balance. I think you can say to him nearly exactly what you wrote to me and ask for his support or help in holding you accountable for the things you set up for yourself.

You’re on the road to what we’d all love to have and we wish for our favorite people: a healthy relationship with your partner and yourself. You got this. Good luck!

Entry 28: May 13, 2019

I met this girl [at the] JFK airport on my way to Art Basel. We hung out in Miami and definitely caught a vibe. Eventually, I realized she was only 20 and still in Uni. I’m 6 years older plus have a very different background. She’s wealthy and Arabic. I’m American and not. I want to pursue her, but I feel like I don’t have a shot. I never feel insecure like this.

While I do wish you provided more context to what exactly catching “a vibe” explicitly means to you, we’ll take it as if you’ve developed more than a crush while spending a few days with her in Miami during Art Basel.

There’s a few things I think it’s important to address here, but to be clear, the ultimate goal is to determine the root of your insecurity and squash it, and I want you to determine what it is you’d like to come out of pursuing her.

Presumably, you and her do not live in the same city, but for the sake of discussion, let’s move forward as if you are looking to be in a relationship with her regardless of location.

While her age could come with characteristics to be wary about (maturity, life experience, what it is she is looking for, etc.), it isn’t 100% indicative that she is “too young.” However, you should be cognizant that graduating from college typically comes with significant life changes and decisions for her to make. For this reason specifically, I’d implore you to only pursue her if you plan on having a level of commitment that would add any undue stress to a very transitional time in her life.

Put some thought into what you want out of the relationship and what that would require from you.

It’s interesting that you bring up your backgrounds and your financial status. Presumably, she’s from money and not independently wealthy at 20 years old. And while there certainly has the potential to be cultural differences between the both of you, I truly think these factors shouldn’t dictate you acting on your feelings. Sure, they could be intimidating in your unfamiliarity with her culture or if she seemed to prioritize money in an unattainable way, but I don’t think these characteristics define her (or that yours define you) in a way that should deter you from going with your gut. Not be all cliché, but ultimately, isn’t it about what’s inside and the chemistry between you?

I’m not dismissing that these differences have caused discomfort in any relationship in the past, but I’m not sure it’s something you need to let stop you from pursuing her. If you end up wanting to propose to her, cross that bridge when you get to it.

Lastly, what is the worst that could happen? Things don’t work out with someone you don’t even live in the same city as? As I mentioned before, I would put some thought into what you want out of the relationship and what that would require from you, but I don’t see any harm in minimally letting it be known you’d like to keep in touch and get to know her better.

Entry 27: April 19, 2019

I’m in a place in my life where I’m dating the first guy that I’ve actually felt emotionally mature and ready for. I’m 26, my last relationship was complete trash, and thanks to this counseling degree I’ve been able to really work through that and move totally different in how I date and what I want in a partnership. Honestly, there are no red flags; on the contrary, just a totally good man. With this guy, there are great boundaries in place, he takes the time to show his appreciation in his own ways, and he has qualities that I would absolutely want in a lifetime partner. We’ve been dating since November and began to date him seriously in February. I know we’re only a few months in but I feel like … I don’t have the intensity in feelings that I would normally have for a guy that I’m in crazy like with. I can’t tell if this is just me being grown and looking at things differently or if, despite him being a great guy, that maybe he isn’t the right one for me. My intuition is telling me the latter, but the logical side of me is like, ‘yo, I don’t think I’ve ever met a man on this caliber’ and walking away because it doesn’t HIT the way I thought it would, would be crazy, because I’ve dated for a few years and a lot of these guys are trash or not ready or not what I want. Will my heart catch up? If it doesn’t, is that a valid reason to walk away?

I very, very, very much understand your question. First, I’d like to point out that you stated all the positive attributes about him that differentiate him from your past partners. You even went as far as to say he is the first guy like this. With that, I’d like to tell you that it is very natural to question the intensity of your feelings for someone or a situation that is decidedly very different from your others particularly in such a healthy way. (I also think it’s notable that you question the intensity of your feelings, but also describe the level of like as “crazy”.)

It’s positive you didn’t speak about him as if you are trying to convince me or yourself, or speak about him in terms of everything he does for you. You see him and his value as an individual, not simply as a partner. So, while you aren’t sure if this forever, it seems you’re still in it for the right reasons.

Truthfully, I don’t know if your heart will catch up. I’ve been in a similar position and wondered the exact same thing myself. As someone who identifies as knowing what she wants and being very decisive, I found myself prolonging making a decision. Then I realized, you don’t always have to make this decision, especially when it’s not black and white.

I do believe this is you being grown and looking at things differently, and despite being a great guy, he still may not be the right one for you. However, if you truly don’t know right now, you don’t need to up and walk away. As long as you are not leading him on, it’s OK to see what happens.

He’s not doing anything to push you into crazy, because he respects you and each of your boundaries.

What you said about boundaries really stuck out to me. I know we sound very bare minimum Twitter about this, but for whatever reason, plenty of men lack any understanding of other people’s boundaries and even less about their own. This could also be the root of why you don’t feel “crazy” in like. He’s not doing anything to push you into crazy, because he respects you and each of your boundaries. That said, healthy boundaries should not equate bored to death.

You’re in a healthy relationship. Take advantage and put the effort to communicate where you’re at.

If you are feeling like he is not “the one,” consider what about the relationship or him makes you question that. Are they things you can discuss? Are they things that can be growth (and not outright trying to change him)? Do you even want them to change? Are they things you’re willing to compromise? Remember, you’re in a healthy relationship. Take advantage and put the effort to communicate where you’re at.

Great men can still not be enough for great women, and as unfortunate as it is, that’s OK.

Ultimately, whether you stay together needs to be based on his and your relationship. Easier said than done, but how trash the majority of other dudes are shouldn’t play a role in your feelings for him. Great men can still not be enough for truly great women, and as unfortunate as it is, that’s OK. Don’t ignore how keen your self awareness is. Not everyone possesses it, and you don’t need to feel guilty if at the end of the day you simply don’t feel it for him.

You should want to be in a relationship you love and want to grow in, and not because on paper it looks “right.”

Your heart can catch up, but it also might not. I’d say put your best foot forward in the relationship. Communicate what you need and want, and if you still don’t feel it, it’s enough of a reason to leave. Will it hurt? Sure. It’ll probably hurt both of you. It’s not easy to genuinely want something to work out that just isn’t there. But at the end of the day, you should want to be in a relationship you love and want to grow in, and not because on paper it looks “right.”

Entry 26: March 29, 2019

Hi Rae, I would love your insight on when to hold on versus letting go of someone. My ex and I have cultivated a good friendship over the past few years. We’ve always said maybe one day we can work things out again, but it just doesn’t seem to ever happen no matter how close we get. He’s still actively dating so it’s obvious he’s looking for a relationship, just not one with me. I never stopped loving him so that rejection is painful. Being friends with him sometimes hurts too. I can’t help but think it’s because I’m still trying to get my life together. While he seems to already have it. Any advice?

From what you’ve said, it sounds like you two are close because you are still in love with him and he still values your presence in his life. But, these are two entirely different things that do not equate to a good friendship.

I really want you to take a look at your friendships — good and bad- — outside of your relationship with your ex. (No comparing them either.) Consider aspects about those relationships you really love, what you put into them, what you get out of them, and how they make you feel.

We’re creating a list of things you should be aware of. Obviously, not every friendship is perfect. People have the ability to disappoint you and hurt you just as you have the ability to disappoint and hurt people. However, if you find your relationship with your ex is completely comprised of justifications, making excuses, putting your feelings last (like when being friends with him hurts), but you continue to engage in the friendship, some action needs to be taken.

Now, I want you to consider the things you love about him. Is it the way he makes you feel? Does he still do relationship-type of things with you? (He shouldn’t, and if he does it needs to stop.) Do you feel like he provides comfort for you to be yourself with him?

You can offer yourself more love than unrequited love ever can.

I need you to understand, you can offer yourself more love than unrequited love ever can. He makes you feel good? Think about that further. He makes you feel good about yourself? You can also find value, if not more, in those things about yourself too, particularly because he doesn’t love you the way you love him.

Someone giving us space to be our true selves is a blessing, and it’s also a step in the direction of being able to do it on our own.

Recently, I’ve learned that someone giving us space to be our true selves is a blessing, and it’s also a step in the direction of being able to do it on our own. You have the ability to be that person with or without him, you just have to accept that as who you are and choose to be, unapologetically.

Finally, the hard part I’m sure you don’t want to hear: It’s important for you to take some space. You very clearly said he’s dating other people and that he doesn’t want to date you. You being in his life this way still affords him the benefit of your presence and all the wonderful things you offer while he shops around for another partner. I’m not even saying you need to totally let go of an idea of a future together, but I do think it’s very important for you to take some space to figure out what, to you, constitutes and is important to a friendship and a romantic relationship.

You’re doing a disservice to yourself by putting your life on hold for someone who is decidedly not choosing you.

You only have one today and you will only have one tomorrow, even if there is some way you do end up together in the future, you’re doing a disservice to yourself by putting your life on hold for someone who is decidedly not choosing you. You’re missing out on growth by holding on to the idea of something that no longer exists. I know it seems like you can grow with him in your life, but I implore you to try to separate yourself and take all the energy you put toward him and invest it in yourself.

Entry 25: March 18, 2019

Straight male, in my 30s and married. Obviously your key demographic. My wife and I am in an open marriage and have been since the beginning of our relationship 10+ years ago. Anyway, I told my wife I was interested in someone at work, she gave her blessing to pursue it. Over the past year, my co-worker and I started with going out to lunch just the two of us, leading to drinks and eventually dinners. She is aware of my marriage’s open status. Toward the end of last year, she told me she wasn’t interested, which I doubted, but respectfully accepted. After that dinner, I made a concerted effort to keep our interactions platonic. Over time, however, things got flirty in the office again, with her asking to go on coffee runs together and exchanging texts after hours. I told my wife about how it seemed like things were picking back up with her and she suggested I get her something small for Valentine’s Day. On the 14th, the flowers were delayed, but I left a small gift bag with her favorite bottle, her favorite gum and a small gift that I thought suggested some thought/consideration on my part. I texted her that I left something small on her desk and the day finished with no interaction. The next day, the flowers arrived but neither of us mentioned it. However, on my way out of the office, she approached me asking if I wanted to take the flowers back. Puzzled, I replied that they were for her to do what she pleased. On my commute home, she texted me asking if it would be OK to leave the gift bag on my desk because she doesn’t think she can keep it. I said sure and apologized if I had messed up or made her uncomfortable and that that wasn’t my intention. The weekend passed with radio silence and our first day back at the office together, I am talking with a co-worker about working from home because of the impending snowstorm and she inserted herself into the conversation to make a harmless joke about me being a slacker. It didn’t bother me, but I will say that I am still a little embarrassed/confused about how to move forward with this and why she would go out of her way to make the joke. My wife thinks she is interested, but is playing games. I’d love to hear what you think.

I want to start off by saying it takes a high level of security, honesty, and maturity to be in the relationship you’re in with your wife. It’s clear you two are married because you have a bond that is rare to find. That said, unfortunately, no matter how crystal clear your communication is with someone else that appears to be mutually interested, the reality is that not many people are capable of or are interested in this level of transparency, or in being involved with someone in an open relationship, or in being in an open relationship.

While I wouldn’t doubt she (your co-worker) is intrigued or has an attraction to you, there was a significant discrepancy between her words last year (she isn’t interested in being involved) and her actions following (coffee runs and after hours texts), and there has continued to be from when she turned down your gift to making a snide remark in front of a co-worker.

I do think it’s natural to deduce she’s playing games, however, I don’t think it’s worth your time or energy to continue to engage in them for two entirely different reasons …

First, your job. As someone who has definitely been involved with co-workers against the advice of every human, the likelihood of things getting messy is greater than everything remaining corporate office chill. If you didn’t feel that way before the gift, rejection, and silent weekend, her insertion in a fairly meaningless conversation about logistics to take a petty and presumably unwarranted to shot at you after changing her typical behavior or texting you on weekends is immature. She’s toeing the line of being a liability to/at work. Considering your high-level of communication skills, I definitely think this misguided shade should be addressed. I’d probably take the route of asking if I did anything that she was retaliating at by making that comment, and I would not allow her to feel like I’m making a big deal out of nothing.

Second, and probably more importantly, it’s pretty clear you guys are not on the same page, which as I mentioned before, doesn’t mean she doesn’t have a thing for you; it means she is not a person comfortable with being involved with you in a way that fits your lifestyle. You can ask, but considering how you’ve expressed she’s handled things thus far, I wouldn’t hold on to the idea of getting an honest response.

I understand you not wanting to fully abandon the idea of something happening between you two in the future, but I do think it’s time to set your own boundaries. Consider the things you and her did or the actions that let you believe you were moving beyond being platonic friends and cut back on those. Playing games or not, she is giving you mixed signals and kind of being a jerk about it, so I think it’s time to create space.

Entry 24: February 28, 2019

Is there such a thing as mixed feelings? A guy friend I had that lives in a different city came to my town and we ended up hanging out the whole weekend and sleeping together. Then when he went back home he was super dry (responding to texts slow or not at all, and in response to a merry Christmas text from me he said “thanks”). I figured I had expressed my interest and he didn’t reciprocate so I moved on, but then he started hitting me up again around my birthday. I was in his city shortly after and we made plans to hang out but then he stood me up and never explained or apologized. Since then, he’s been interacting with me on social media like nothing happened. I ignore him. What do you think this all means? What do you think I should do? He knows I’ll be in his city again in a couple weeks. If he hits me up again (I think he will), how should I respond?

First, let’s address your initial question. Yes, there is such a thing as mixed feelings. Have you ever tried those lime tostitos? They’re weird at first, then you aren’t sure if you like them, but you keep eating them because you are trying to determine if you like them. I like to think of mixed feelings more as something you are on the fence about but keep engaging with to determine if you are down or not.

But, even for those that think mixed feelings manifest themselves into mixed signals and being present sometimes and not others, I can’t argue against it. I can just ask you, even if that is what this is, do you want to deal with someone who is in a perpetual state of indecision about you?

I do not think your boy has mixed feelings. I think all of this means he’s selfish and self-centered. He’s probably the type that doesn’t want a relationship or want sex to change things between you, but he’s the one that’s allowed it to by changing the way he communicates with you — from as his friend first to now as if you’re an afterthought or someone he is genuinely uninterested in. There’s no need to decode here. Take what he’s showing you literally.

Let’s look at it like this, if someone you hadn’t slept with switched up on you from being a real friend to not responding, saying “thanks” to well wishes rather than reciprocating, and outright blowing you off without addressing, would you not look at them funny and question where they hold you and the friendship? Hold him to that same level of accountability.

He is showing you that he does not care. Inaction is an action.

He is showing you that he does not care. Inaction is an action. Silence speaks volumes, and this dude lacks empathy or the ability to care how his actions are received and effect others. This is zero reflection on who you are or how you’ve treated him (according to what you’ve shared), particularly since you said you indicated you were interested and were left with impression he wasn’t, so you kept it moving.

I can tell you what I think you should do, but it’s really about what you want to do. I believe your best options are to continue to ignore since that’s already what you’re doing or if and when he hits you up (because he’s in town) ask him why he thinks you’d make time to see him after he blew you off the last time you made plans. Personally, I’m extremely committed to holding men that I’ve been intimate with accountable, but you’ve already maintained you don’t need to engage with him so it may be worthwhile to continue to ignore him.

His “likes” can’t be contributing anything that inspirational to put up with someone that engages with you only when it works for him.

Further, not once did you say you were that into him throughout your entire note. I don’t think he’s worth your time since he’s blatantly disrespected it. His DMs and IG “likes” can’t be contributing anything that inspirational to your life to put up with someone that engages with you only when it works for him with total disregard for you and your time.

Entry 23 | February 8, 2019

My boyfriend “likes” thirst traps on IG. He says the girls are his friends, but I’ve never met them. He has me on his grid and on his story tagged, but I still don’t like it. What should I do?

This is not going to be easy to hear … This screams trust issues. (If I could put the iMessage invisible effect on this I would.)

It is very normal for your significant other to have friends (of any sex) that you have not met and vice versa. Does he know all of your friends? It is virtually impossible to spend every waking moment together or to meet every single person your significant other knows, is acquainted with, or is friends with. I’m sure he has family you haven’t met, but that doesn’t mean that they don’t exist.

If these women are his friends, it would seem a little suspicious to avoid liking photos that may be deemed thirsty. If I put myself in his shoes and if a friend posts a photo where they feel good about themselves and how they look and it’s very apparent, I will like it. I want them to feel good about themselves and as a friend, I’m here to acknowledge that. So, I’d like the photo.

Would it be different if he was liking photos of attractive girls he didn’t know? I kind of think this idea that he shouldn’t like sexy photos of girls he is friends with furthers the false narrative that heterosexual men and women cannot be friends without sex being at the forefront of the relationship or that him deeming someone attractive means he does want to be intimate with them.

It is possible to be in a committed, healthy, and monogamous relationship and find other people attractive without compromising the relationship.

It seems as if you don’t believe they are his friends. To that I say, even if they aren’t close friends (which I’m unclear of if they are or aren’t) it is also very likely that both you and your significant other will find people of your desired sex attractive no matter how long you’ve been together or how many times you’re on each other’s socials. Honestly, I think it’s absurd to hold on to the notion that while in a relationship you can’t acknowledge another human outside of the relationship is attractive. It is possible to be in a committed, healthy, and monogamous relationship and find other people attractive without compromising the relationship.

I think I can understand this being bothersome if he only liked overtly sexy photos of other women, period. He likes photos of his women friends on a platform he makes it obvious you are his girlfriend. If you believe these “likes” are a sign of disrespect and translate to malintent toward your relationship, perhaps there’s a bigger issue in the relationship.

The bottom line is you need to figure out whether or not you secure in your relationship and do you trust him? The fact that you know what he is consistently liking on Instagram tells me you may be looking for something. If the trust is broken from a prior instance in your relationship, this makes sense, but I wouldn’t make this the foundation of questioning his dedication to you.

Entry 22 | January 22, 2019

How should I ask my partner for alone time? I haven’t really found a way to ask without her getting defensive or offended. We’re not in a long distance relationship, but we don’t live a super convenient distance from each other. I spend about half my week at her place and she comes to mine for a night or two on weekends. There’s nothing good online to show how to discuss it and my therapist and I have quite found the right words to communicate it to her.

Being that you consistently spend multiple days at a time together, it seems like a natural request. However, it also appears as if alone time is not something she holds as a priority herself or over time with you. This is fine, but I think it’s important to recognize that you two differ, on this topic, as it will be something you want to bring up when you discuss this.

Communicate that spending time alone has nothing to do with being away from her, and everything to do with being alone with yourself.

That brings me to the plan: Undoubtedly difficult, I think it’s time to address your singular request as a bigger obstacle. You need to communicate that at the core of this, spending time alone has nothing to do with being away from her and everything to do with being alone with yourself. This is no longer about being separate for an hour, this is something you’ll want to do consistently and do not want to hurt her or fight her about it every time.

I think you could address the few times you’ve asked for some solo time and how she responded in the same breath by asking what you could do to ask differently or make her understand it isn’t personal. While she has taken it personally in the past, offering her some input or even control in the situation may change her response. Another uncomfortable, albeit surprisingly under utilized question, you can ask her is why or what about the idea of your alone time upsets her? Do not ask it in a dismissive way. Reassure her feelings are heard, but you want to understand and in turn you need her to understand by gaining clarity on her discomfort.

Share why you value your alone time … shifting the focus from you leaving her to you investing in yourself so you can always bring your best self to the relationship.

You also may want to share with her why you value your alone time and what makes it important to you in hopes that she could see outside of her insecurities and understand how much you value it and why. This may help with shifting the focus from you leaving her to you investing in yourself so you can always bring your best self to the relationship.

While you really should not be in a position where you need to justify spending some time by yourself, I think it’s necessary to ask her to accept that this is important to you. I firmly believe that self-centeredness is rooted in insecurity. While you do not need to say this to her, the reality is she’s only thinking of herself. I also have a STRONG preference to relationships where parties hold on to their individuality while being fully committed to each other rather than functioning as one. You may want to consider the big picture of your relationship and have a discussion about things that are important to you (alone time being one of them) as your progress. Don’t forget that a relationship progresses as you learn about each other more deeply. It isn’t unnatural to experience growing pains.

A relationship progresses as you learn about each other more deeply. It isn’t unnatural to experience growing pains.

Lastly, alone time should mean alone time, not you magically ending up out with the boys because it wasn’t planned time. I get the idea that this is not the case, but for anyone else that has utilized the concept of alone time as just to get away from their significant other.

Entry 21 | January 4, 2019

My partner says they’re open to threesomes, but I’m not under any circumstances. Am I being unreasonable?

Interestingly, our last question was around how to ask for an open relationship. While a threesome and an open relationship are different, ultimately each situation is bringing new parties into a monogamous relationship.

The dictionary definition of “unreasonable” is not guided by or based on good sense. You are not being unreasonable and your partner should not make you feel like you are. For the same reason they are open to it, you are not. These are preferences and yours differ on whether or not you want to have a threesome or not.

Although simply saying no is enough and is not unreasonable, since you are in what appears to be a monogamous relationship, communicating why you are opposed will only lend for better clarity. While this may take some potentially uncomfortable vulnerability on your end, communicating why you are not into a threesome together should offer your partner more than enough reason to accept your decision. If you’re having trouble finding the words consider offering reasons like you’re only interested in being with them, you are not interested in sharing your partner, and you are not interested in sharing yourself with another person outside your partner. If it is because you don’t like the idea of someone outside of the relationship being with your person, say that. If you are insecure about it, that’s OK too. Don’t hesitate to be honest.

You can ask them why they are open to threesomes as well if you’re interested in understanding, but try to pose it as exactly that — a desire for clarity — rather than defensively.

If they are making you feel unreasonable or wrong by pressuring you and not respecting your decision, you should tell them that. This isn’t a negotiation. You wrote that you’re not down with a threesome under any circumstances. That doesn’t sound like you’re flexible and an idea that you can or need to be worn down into; trying to change your mind shows a lack of respect for your decision.

Finally, while I don’t know your age or priorities, I think you both should consider how important this is to each of you and determine if this will be a deal-breaker. It’s OK to have different preferences, but if you’re partner refuses to live without threesomes for whatever reason and you refuse to have one this may cause some changes. While this absolutely does not need to be a deal-breaker at all, they might be better off with someone who is open to them and you may be better off with partner that is solely interested in monogamy with you.

Entry 20 | December 14, 2018

How do you have the conversation about having an open relationship with your partner?

This has the potential to go a lot of ways. You’ll want to communicate your desires very thoughtfully which means you must start with yourself. I implore you to assess the status of your relationship. Have you been together for years and it’s healthy but you want to spice things up? Have you been together for years and it’s boring so you want to spice things up? Are you really just trying to have your cake and eat it too?

If your relationship isn’t healthy as it is, entering an open relationship is not going to fix it. You just want to sleep with other people. Break up.

That is not to say an open relationship can’t work. It can, but like any relationship, monogamous or otherwise, the foundation of it should be trust.

If your relationship isn’t healthy as it is, entering an open relationship is not going to fix it.

Next, you’ll want to choose your words wisely so it isn’t misunderstood. The empath in me really wants you to consider all the ways this could be taken. You do not want your partner to feel like you are desiring this because they aren’t enough. You’ll want to position it more as a journey you’ll embark on together, that they are your priority and show that you’ve put thought into the type of boundaries you’d have.

Consider boundaries and discuss them before you start adding people to the mix.

Yes, you need to consider boundaries or “rules” even, and you’ll want to discuss them before you start adding people to the mix. Some examples could be not sleeping with people you’re both friends with or if you both travel for work, not seeing other people in the city you both live in. You’ll cross this bridge when you get to it, but it is definitely something to consider before you bring it up. There is a lot of value in thoroughly thinking about what you’re asking for before you ask it for you and your partner’s sake. Besides, if they’re interested they might have questions, and you’ll want to be prepared to answer them.

Check in before you ask for this big change because it has the potential to significantly change things no matter the outcome.

I think it’s worthwhile to ask them the questions you asked yourself. This will show you are invested in the relationship and not just sex outside of it. Check in before you ask for this big change particularly because it has the potential to significantly change things no matter the outcome, open relationship or continuing to be monogamous. Ask if they’re satisfied. Ask if they’re fulfilled. Ask if there is anything more they might want or are interested in. An open relationship isn’t just about you — it’s still a relationship.

Finally, if you’re shooting this blindly with zero clue whether or not your partner may be interested in this, you can find subtle ways to bring it up to kind of gauge where they are at with intimacy with partners outside of the relationship. You can start small and talk about celebs or famous crushes that you would give each other a “hall pass” for. Like should Rihanna ever pursue him or her, you’d definitely be OK with them sleeping with her and you’d want that in return. If he or she reacts adversely or insecurely about it, you may want to table the conversation until you’re at a place where the relationship feels more secure. If they aren’t cool with Rihanna baggin’ you, I think it’s pretty unlikely they’ll be down with someone in the same dating pool spending any time with you.

Entry 19 | November 30, 2018

I met this guy at my job, a co-worker. Since I’ve started the job, him and I have got along and been going out for drinks and food after work. We’ve spent so much time with each other. He’s three years younger than me and I can slowly start to feel and see the differences between us. The thing is, I like the way he makes me feel. He’s different. Last night he told me he wants him and I to be ‘together together’, and I don’t know what to think of it. I liked things the way they were. ya know “undefined.” How do I tell him I’m interested in being together, but not interested in being together, together?

This is much less an issue with him. You need to determine what you think of what he wants, and then communicate to him what you want.

You bring up his age and the fact that you are beginning to feel and see the age difference, but then you follow up by saying you like the way he makes you feel and that he’s different. Is his age a deal breaker, or does how he make you feel and how different he is outweigh that he is younger? Are these reasons you want to be involved and not “together, together?”

When you say “together, together,” do you mean boyfriend and girlfriend or do you mean intimate? You did not indicate whether or not you are sleeping together or simply spending a lot of close platonic time together. There is a significant difference between the two. Whatever it is you want to continue, start, or lessening, determine that and communicate that to him.

You also did not mention him being your co-worker as something you’re wary of. Although, I don’t know your jobs, I’d consider thinking about how the relationship (at any degree — platonic to boyfriend and girlfriend) could impact your job. If you’re head over heels in love, risking your livelihood makes more sense than stringing someone along that you don’t want to be in a committed relationship with.

You need to let go of the way things were and “undefined.” He asked for more and while it does not need to be a definitive yes or no, you need to determine what it is you want and stick to it. If you want to be friends with benefits and no title, communicate that. If you want to spend a lot of quality time together and not be intimate, communicate that. Your question itself was pretty unclear — interested, but not interested.

That said, it seems you are on different pages, and that’s OK. You do, however, need to determine the page you’d like to be on, let him know, and be prepared for him to either be down with your desires or end the situation. If he is special to you, he deserves clarity on where you stand. While it isn’t easy to let someone know you think you want different things, it’ll be even more difficult to live doing something you don’t want and have to deal with that further down the road.

Entry 18 | November 9, 2018

When a long-term relationship falls apart but you take some time and are ready to start over, what’s the first step?

No matter what went wrong the first time, the main problem that exists at this point is the lack of trust in each other. When a relationship fails, trust that your partner will be a good partner has diminished. Ultimately, you’ll need to both be open to repairing and regaining trust in the other person and you yourself being trusted.

It’s important to examine things you did that negatively affected your relationship, take responsibility for them, and prepare to adjust.

That said, the first step starts with you. I think it’s important to examine things you did that negatively affected your relationship, take responsibility for them, and prepare to adjust.

While it will be instrumental to leave the past in the past, it will be even more beneficial to address the past, discuss how changes can be made by both parties, and commit to those changes. In order for it to work, this has to be a new chapter and it cannot be simply a repeat of your first shot at a relationship.

Discussing what went wrong in the time you spent together will be challenging. Expect that. It will be easier on each of you if you both use “I” statements rather than “you” statements when tackling the past. Rather than saying something like, “You always did this to me,” you’ll want to be very conscious of how you put your words together to not sound accusatory. Try saying something like, “It made me feel insecure when this would happen repeatedly” or “I don’t want to have to question how you feel about me when these things take place.”

If you really want to make it work, communicating each of your needs, desires, and gripes will only help build a stronger bond.

Be conscious of how you give and receive feedback. The end goal is to be together. Try to view them as things to work on or change rather than accusations or criticisms. This should help you receive them without your pride getting in the way, and it should help you find the words to say to your person. It won’t be easy to say the things you didn’t like about the old relationship, and it will be even tougher to hear what you contributed to the fall out, but if you really want to make it work, communicating each of your needs, desires, and gripes will only help build a stronger bond.

Finally, make sure you leave this discussion with feeling settled. This is where you put EVERYTHING on the table in hopes to leave it there. It’s time for a new foundation and you don’t want to start to build it on unstable ground or be rooted in past hurt. Talk about it then put it behind you.

Entry 17 | October 19, 2018

I was in Austin recently for a conference when I opened up Bumble in search for some southern hospitality for the remainder of the weekend. What was meant to be another work trip hookup, turned to be one of the best first dates I had in a long time. (I’m a New York native, who has been single for seven years and counting, so I’ve been [on] a lot of dates).

He’s a Ph.D. student at UT, on the professor track for sociology and economics. Not only did we connect sexually and mentally, he also has the characteristics that I’m looking for in a partner for long term compatibility. The biggest thing that stood out about him (aside from his dick), was that he was genuinely interested in me, my career, and impressed by it.

We stayed in contact and the other week he hits me up with “Hey, you should come back to Austin.” Learning from past experience, I withheld my enthusiasm asked if he had a ticket. I didn’t expect him to offer because I know I make more money than him, but he should at least try since he’s the one inviting me back. So he did, and I proposed even splitting if to make it fair. He says he’s looking into it.

My question is, do I even entertain this? My head says this is over because of practicality. I did read in one of your recent ILY column [entries] how dating in NYC is so hard and people often end up in long distance situations, which I have seen happen to my friends. I wrote “must live in the same city as me” as a deal-breaker, but now I’m wondering if I should make the exception.

I lived in NYC for almost my entire life, after immigrating with my family as a baby. I have yet to try another city and I know Austin would be a good option career wise (I work in media and tech). I have been thinking about relocating once my lease is up, before I even met this guy, and with other friends leaving now I’m starting to wonder my time is approaching too.

Right now I am following the money in terms of my career, and the rent is too damn high in NYC. I also need to follow my heart, but I need to come to a compromise … What do you advise?

OK, let’s start with your first question on whether or not to entertain this trip. My thought process is usually a checklist of differing levels of asking myself what’s the worst that could happen? You could go and realize he is not as appealing as you thought. You could go and it could be your own modern day fairy-tale. You could also not go and keep your ass in New York changing and risking absolutely nothing.

Some insight: once upon a time I vehemently avoided this man I was VERY into for a myriad reasons with the top three being he didn’t live in the same city as me, the nature of his job wasn’t something I wanted to get wrapped up in, and he appeared like a certified life-ruiner. After over a month of hearing from him consistently and realizing the level of inconsistency I was dealing with attempting to date men in New York, I just gave in. Worst case scenario? A little potential heartbreak? It worked out fine. We had fun. We argued. It ended. Time passed. We became friends. [Shrugs]

You said it yourself: you are interested in him. You are single and without prospect in New York. The trip is worth it. It’s everything else you’re talking about that requires a little more mindfulness.

I can’t front though, you’re immediate mention of moving to Austin is a tiny bit worrisome. Pump your brakes. I don’t think you should even entertain the idea of moving before seeing each other again. While you don’t need to have a hard plan you are going to commit to today, you’ll want to think of some things to consider once you see each other again like, would you try long distance, would you try an open long-distance relationship, will you make plans for him to come to New York, etc. These are just a few things you’ll want to be prepared to think about (and eventually talk about with him) after spending some more time together, much before you consider moving to another city.

The person, out of the two, without any foundation of friends is faced with the challenge of making a life for themselves in a new city.

One other thing I will mention about moving to a new city where your significant other knows more people than you, it can be challenging. From experience and from friends that have done it, the person, out of the two, without any foundation of friends is faced with the challenge of making a life for themselves in a new city where they can easily adopt their significant other’s friends, favorite restaurants, favorite bars, and whole entire lifestyle. When these relationships end, their the person to almost re-familiarize with a new city minus a big part of the life they’ve built parallel to the other person who already had a foundation. This obviously doesn’t always happen, but as someone who’s moved to two major cities — one with a significant other who had no friends where I had a lot and to another single — this is an unexpected challenge we faced, and I’d want to mention it with how open you seem to be moving.

Be honest with yourself about your feelings and what you’re willing to put into it.

Regardless, you recognize that there is something different about how you feel about this guy than others, and I think that’s enough reason to invest a little time in getting to know each other better. The key is to be honest with yourself about your feelings and what you’re willing to put into it so you’re comfortable being up front with him.

Entry 16 | October 5, 2018

How do I stop projecting my shitty dating experiences on to my friends?

I’m going to keep it one hundred with you: this is going to take a deep self-examination. Projecting your unsavory dating experiences on to your friends’ relationships comes from your insecurities or the hurt you hold from when you found yourself displeased with the outcome.

Projecting your unsavory dating experiences on to your friends’ relationships comes from your insecurities or hurt.

Albeit easier said than done, try to look at your “shitty dating experiences” individually and not lump them all together as just having overall bad luck with dating. Look back at each circumstance differently and consider your part in the relationship and subsequent falling out. Don’t take responsibility for EVERYTHING that went wrong, but definitely consider where you can take responsibility for things leading up to the bad. From there, promise yourself you’ll handle things differently should a similar feeling or circumstance with a new person in your life arises. Commit to a plan of how to healthily address these situations and adjust your past behaviors. Now repeat this for all the shitty dating experiences.

Remind yourself that there is nothing you can do to change the actions of the other person in these relationships, too, while not putting the whole blame on them. In the future, go in to dating recognizing you don’t have any control over what someone does. You can only control how you act and how you react.

Go in to dating recognizing you don’t have any control over what someone does. You can only control how you act and how you react.

Ultimately, this is a process that will allow you to let go some of the traumas or pain from past heartbreak that’s caused you to project on to your friends. Projections tend to come from our own insecurities, so once you’ve worked out the root of this prolonged disease, it’ll be easier to not look at your friends’ relationships through your own hurt-tinted glasses.

Finally, coming to a place of security with yourself and self-love will have you look back on these bad memories in your dating life as their other person’s loss, just bad timing in your lives or it simply didn’t work, which is OK. The majority of people you date are not going to work out forever if you want to end up with one person. With acceptance, a plan, and confidence in yourself to do what works best for you without damaging future dates, you’ll have a different outlook allowing yourself to truly be there for your friends through the good and bad going on in their dating lives.

Entry 15 | September 21, 2018

I’m a year out of a long-term relationship of four years and tired of dating. Is it ever too soon to dive into another relationship?

The answer to your question is yes, there are definitely times it is far too soon to jump into another relationship. While I’d prefer not to put a definitive time frame on the number of days, weeks, or months you should wait before getting into another relationship. Time is important, but what you’re doing with that time post long term relationship is far more important.

There’s a lot of personal growth that happens in a timespan of four years with someone. You’ll want to put in the time to relearn yourself, and solo, before diving into another situation where you need to accommodate someone else’s needs and wants.

Go to your cousin’s wedding dateless or with a friend. Listen to whatever music you want. Change your mind. Pick up some new hobbies. Pick up some old hobbies. You are going to have an influx of time and a lack of second opinions to listen to. TAKE ADVANTAGE OF THIS TIME.

You’ll want to put in the time to relearn yourself, and solo, before diving into another situation.

Purely from the amount of time some of these things will take — a few weeks is not enough time — and more often than not a couple months isn’t either. This doesn’t mean you shouldn’t date. This means you should not get into anything serious, and let me be crystal clear: Not getting into anything serious does not mean you fall into the same routine as having a monogamous relationship but without a title. Not getting into anything serious means no matter how much fun you’re having with a new person, you, your friends, your family, your job, and maybe even acquaintances should come before this budding relationship. Be transparent, up front, about what you’re getting out of and what you’re looking for or not looking for and stick to it. Keep your wants and desires in the forefront.

Not getting into anything serious does not mean you fall into the same routine as having a monogamous relationship but without a title.

For you specifically, having put an entire year between your breakup and being open to something more serious does seem like enough time, however, if I can be honest, it almost sounds like you’re into the idea of a monogamous relationship through the exhaustion from dating. I have news, you’ll have to continue to date in order to find someone you want to take serious, but I do believe a year is enough time. (Just take a look back on your year and establish yourself as an individual.)

Be transparent, up front, about what you’re getting out of and what you’re looking for or not looking for and stick to it.

I believe you can easily get familiar with yourself as an individual in a yea’s time following a LTR, but (unfortunately), you’ll need to continue dating to find someone that’s a good match rather than just throwing your hands in the air and settling for the next person that walks through the door.

Entry 14 | September 7, 2018

Is waiting for marriage to have sex a weird thing to do in 2018?

I wouldn’t call it weird as much as I’d call it an option or a choice. It may not be the desire of the majority to do so, and I think it will diminish your dating pool significantly but a smaller dating pool isn’t necessarily a bad thing. However, because it doesn’t seem to be the norm, you may want to find the words to communicate why that’s your preference and if it comes with any expectations of the person you’re dating. If you are a virgin, do they need to be one as well? Do they need to abstain throughout your relationship? Are you waiting for marriage for religious reasons? Because it isn’t the norm, you’ll want to be keenly self aware to why you’re waiting and understand what you’re looking to achieve within a potential relationship with this choice.

Now, had you asked if I thought you should wait for marriage, I’d tell you absolutely not. I would never say sex is not a big deal and to knock it out before you get married. On the contrary, I find that sex and physical chemistry is such a big deal that it’s normal for that to be an aspect of a relationship that not only requires communication but work and a level of seeing eye to eye. Thus, without having intercourse with your significant other, there may be topics you don’t know how to navigate until you’re married, and like any other thing on the planet, practice makes perfect.

Further, I firmly believe that a high level of maturity allows for being in the right head space to commit to someone to be in a monogamous relationship and eventual marriage. For this reason, I also believe that experiencing sex before you choose to marry someone will allow you a higher level of growth than entering a lifelong commitment with someone without having done it, particularly since traditional marriages include you having sex with only your spouse until death do you part.

Your relationship with yourself is priority and is only immediately followed by the person you want to marry, and being on the same page is pivotal into building a strong foundation.

If you choose to abstain, I’d make sure you’re still comfortable talking sex, pleasure, and physical desires and not to avoid discussing it simply because you’re choosing to wait until you’re married. These will be things that come up when you’re tied down and you’ll want to know you and your partner can talk through them before committing.

Finally, recognize that this decision is about you and for you. You shouldn’t come to this conclusion to appease someone else for they will not be a part of your relationship. Similarly, you shouldn’t let someone else pressure you into having sex if you firmly want to remain abstinent until you are married. Your relationship with yourself is priority and is only immediately followed by the person you want to marry, and being on the same page is pivotal into building a strong foundation.

Entry 13 | August 17, 2018

I’ve found something really special; like, ‘speak secret language with each other’ special. We’ve hashed out a lot of back story over only two days of being romantically involved. (I knew of her [before].) My brother says because she’s “cleaning my face while I’m eating” and [we’ve] had a conversation about her “figuring out what we are” that she wants to be my girlfriend. We understand we’re being exclusive right now, after she made me breakdown my feelings. Should I be texting her like, “Hi my beautiful/pretty girlfriend” already? Or not, and just wait till there’s a “great ass moment” in the next week(s) to make it more of a statement? Or both? I’ve told her I don’t want to put her in a position to overcommit and be in a pressured situation.

You sound like you’re in love which is beautiful. That said, I’m a huge fan of pumping the brakes. I do agree with your brother; she’s definitely into you but more so because you’ve discussed your feelings, intentions, and exclusivity rather than simply going off the cute, doting actions. Finding someone you feel like you have a secret language with leads me to believe you feel very understood and safe and that it is seemingly reciprocated.

Enjoy it.

Something I’ve asked multiple friends that ask me “should I be feeling this” or “should we be doing that” is, is there is a set of laws for dating I’m wholly unaware of? Lose the idea of what you should and shouldn’t be doing when it isn’t in terms of things that are illegal or morally wrong. Focus on how you feel, how she feels, and how you want to make her feel rather than mincing good morning texts.

However, I do not think it makes sense for you to address her as your girlfriend without discussing titles or the relationship. It’s presumptuous, particularly if you are concerned about pressuring her or putting her in a position. I’m not saying she isn’t down. I’m saying if you have such a comfort with communication, talk about it first.

You seem a little nervous, but it also seems like everything is going really well. I really, really think you should continue on this path of getting to know more about each other as you are not seeing anyone else and let yourself feel less pressure about a title. You can always text her “Hi pretty” rather than “Hi, my pretty girlfriend” as much as you can wait for a great moment to express your admiration and value in her.

Not that there is a “right” time, but when the time comes where this nervous energy subsides ask her to be your girlfriend. Do not just call her that suddenly. Ask her. Right now you’re in a good place. Try not to put too much pressure on yourself, and remember to switch those feelings of what you should and shouldn’t be doing to focusing on what you want and what she wants.

Entry 12 | August 3, 2018

Where do you draw the line between being petty and taking the high road? I was just dropped today for someone else in her rotation since it was “getting serious.” I always feel like the right move is to take the high road.

In the long run, taking the high road usually warrants better results. However, I can’t say I’ve personally never taken a low shot. In this particular instance, you should opt against taking the petty route. You’re not going to look like anything but bitter and hurt to both parties.

If the circumstances were more like you and her were in something committed or exclusive, I could understand your desire to let her new guy know she was playing both of you. That does not seem to be the case. You said yourself you were dropped for “someone else in her rotation” because it was “getting serious” with the other person, indicating that you knew you were not the only one and that she didn’t lie to you. To be quite honest with you, this doesn’t really sound like being petty at all. It sounds like you’re hurt, and hurt people hurt people. Further, if she does in fact have a “full rotation,” even if the guy she chose over you decides to drop her, it seems like she’ll have a back up.

Finally, I have to ask, what would you gain out of reaching out to the other man and what you would even say to him? I have reached out to the other woman in the past, however, I was in something that I believed was exclusive and found out I was being lied to. I also knew they were in bed together and wanted her to wake up next to him with the truth. Did it hurt both of them? Seems so. Did they continue to date still? Yes, for a bit. Did I gain anything from it? Not really. I’m positive I looked bitter and hurt, but I also was being bold face lied to, specifically while she was physically next to him. That woman did not do anything to me and was kind of a casualty of his actions and my hurt. This woman, who you dated, did not do anything to you, and her guy she’s getting serious with did even less.  

I think you need to really be honest with yourself, figure out if your feelings are hurt or your ego is bruised, process those feelings, and consider communicating them to her. It’s OK to feel bad about rejection; it’s not OK to treat someone who respectfully ended things with you with malice and ill intent. It says a lot more about you than it does about her.

Entry 11 | July 20, 2018

How necessary/effective is it to play hard to get?

Personally, I think the concept of “playing” or pretending anything is useless; however, a lot of people have proven that in order to not make themselves entirely available to new people in their life that exhibit a bit of potential to be something more, they have to play hard to get.

You can treat them special while still maintaining some semblance of your existing life.

I implore you to think bigger than this, and to think about yourself more than this. Rather than playing hard to get, why not just not make this new person a huge priority from day one? There’s value in maintaining a sense of self when a new person enters your life. To be clear, don’t say no to their requests to see you for the sake of playing hard to get, say no to their requests to see you because you have a goddamn life and responsibilities. You can treat them special while still maintaining some semblance of your existing life. You can move forward while not being totally available, and that’s OK.

This will allow you to set realistic expectations from jump. If you’re going above and beyond, giving this person all of your time, there may become a point where this will be hard to maintain. Conversely, if you’re playing games from day one, you will build a foundation of communication that’s based on what you think they need or want rather than what you need or want. A happy medium will naturally allow you to be kind of hard to get without it being faked or forced. Further, if you’re faking hard to get and then stop, I think it’s safe to assume this person will pick up on a shift in your energy, and although you’re being more honest it could come off as a change that needs to be questioned.

If playing games is what this person requires to be with them, you need to decide for yourself if they’re even worth it.

Finally, if playing games is what this person requires to be with them, you need to decide for yourself if they’re even worth it. We all enjoy a little excitement, sure, but that can come from you genuinely being unavailable rather than pretending you are and then sitting at home checking their IG story every 36 seconds wondering what they’re doing.

Entry 10 | June 29, 2018

My ex that I lived with, discussed babies and marriage with, and spent over three years with is engaged to a girl after meeting each other twice (our friends told me). Granted, his family essentially made him choose them or me. In hindsight, they would’ve made my life with him a living hell as I don’t practice their religion and they never accepted us together. For awhile, he let me believe we were in it together. But instead of getting engaged, he broke up with me. We don’t speak anymore, and I don’t think I want to see the upcoming engagement party my friends alerted me of. Can I unfriend him on socials and what does that look like? Do I look weak?

What does that look like to who? It’s likely he is who you are concerned about noticing. I say do it. I actually highly recommend it, but we are all ready to fully cut ties at our own pace. There are definitely some things to ask yourself to help you come to this decision.

What are your concerns about doing it? Does it matter if you look weak in the eyes of someone who was incapable of dictating and carrying out his own decisions with honesty? Ask yourself if you want to speak to him again. If not, cut the ties. If you do, ask yourself why. If it is vengeful and angry, I’m going to go ahead and recommend unfriending him, too.

Let me make this crystal clear. You do not owe him ANYTHING. You are allowed to be sad. You are allowed to be mad. You are allowed to not want to be his friend in real life and/or online. Matters of religion and family are to be discussed (key word) ideally with an open mind and honestly (key word), but if he let you believe he “chose” you when his family was the one that imposed making a choice on him only for him to change his mind years down the line, you have every right to not want to speak to, hear from, or see anything about him indefinitely. You don’t have to run the “I’m OK” campaign by maintaining connected to him. It sounds like you’re trying to prove you’re OK to someone that hurt you who you have zero intention of speaking to at the end of the day thus making it a huge waste of time and energy. Hit that delete friend button, girl.  

If you think somehow you can be friends, this is probably the only way I’d say stay connected, but I’ll also tell you I don’t believe you. You can keep it 100 with me, you just want to drag yourself through the pain of it all and lurk. As much as I’d advise against it, it’ll only be a matter of time before indifference sets in and you cut it or seeing anything about him will leave you feeling unaffected, because the bottom line is he is living for someone besides himself, his family.

Finally, if it’s for the sake of your pride, do yourself a favor and mute him on every platform possible and don’t leave any digital evidence of checking for him.

Entry 09 | June 1, 2018

For background, me and my ex-gf were in a year long long-distance relationship. Things were well but over time the distance would be the end to our relationship. We still cared for each other but couldn’t bear the complications that come along with long-distance. When we decided to go our separate ways, we agreed that if and when we were ever in the same city that we would try to work things out. So fast-forward a few months and I end up back moving to our hometown, unexpectedly, and our relationship had no bearing or influence on my move. It was a matter of being unhappy in the city that I was previously living in (DC and Donald Trump was my unfortunate neighbor). Now that I’ve been home, we’ve only met up twice and the distance has stayed even though our proximity is closer — which is unfortunate but maybe that’s the way it’s supposed to be. I still care for her and would love nothing more to get together again. After many failed attempts and her flakiness, I think it’s time for me to move forward — but it’s tough when I still care for her. Am I not respecting my own worth and value?

Have you flat out asked her to consider getting back together? (I know this may leave you at peak vulnerable because you may get an answer that you’d rather not hear.) That said, considering her actions and the nature of breakups, when asking something so direct (especially from someone that’s been flighty), you have to come to terms that she may not give you an honest answer if she offers an answer at all, but you will know that you tried and you were honest about where you stand.

Also, homecomings can be weird. While you were gone living life in a bigger city, the dynamics between old friends and your own relationships may have changed. Obviously, you had your heart set on a fresh start with ol’ girl, but this is a time to focus on you. You made the move to a bigger city once, do you even really want to live at home? Or was it just D.C. that wasn’t for you? Reflecting on what you want for you and your life outside of the relationship (or any other relationship for that matter) will shift your focus to your worth, your value, and the direction you want to take your life in.

I’m not sure you are at the point of not respecting your worth and value — not to diminish your feelings or her lack of ability to keep it one hundred. Her silence or the assumed lack of value she has in you or the relationship does not bear any weight on your actual worth or value and you need to never forget that.

I do think it’s time for you to consider moving forward. I’d recommend against jumping into anything serious with anyone else right now, as it could easily end up picking up where you left off with her but with a new body in her place. But don’t shut yourself off completely from dating. Just because you’re moving on now doesn’t mean your future selves can’t get together again. It just seems like now you need to focus on you and your life without her and see what good things you create for yourself back in your hometown after some time away.

Entry 08 | May 18, 2018

What is the difference between compromising and changing for someone? I think it’s a fine line and that people are adamant about, “This is me and my rules, take it or leave it.” That seems to only work if you really don’t care about each other, but on the other hand people have lost their whole identity in a relationship.

There is a very fine line, because the reality of any relationship — romantic or not — is that there will be give and take and a level of sacrifice. That said, it is also very true that there is something taboo about maintaining independence once you become half of a couple. This is a social norm that I personally cannot get on board with, specifically because it’s not rare for some relationships to look a lot more like a dictatorship than love (or lust, even). And you’re right, specifically in those circumstances, if you are so adamant on having your way or the highway, it’s likely you don’t care that much about the other person or anything outside of yourself. Selfishness and independence are not the same.

The word compromise even has kind of a negative connotation to it, but compromising is normal, necessary, and not the same as changing for someone. By Merriam-Webster’s definition, a compromise is “a settlement of differences by arbitration or by consent reached by mutual concessions,” “something intermediate between or blending qualities of two different things,” and “a concession to something derogatory or prejudicial,” but to say compromising in a relationship is negative is unrealistic and likely from a place of selfishness.

Being independent and being in a relationship are not two mutually exclusive states of being and can coexist.

While the crux of compromise is altering what you want, the reality of a being in a monogamous, romantic relationship is you will need to think outside of yourself when it comes to wants and desires, in addition to how your actions affect your person. However, being independent and being in a relationship are not two mutually exclusive states of being and can coexist. If you never want to compromise or be open to compromise, you should consider being single for life, because it is that mindset that will cause a partner who may have a weaker identity to lose themselves in you or the relationship or change for you.

Losing yourself in the relationship happens when only one party compromises. If you do what you like, watch what you like, hang with whoever you like, eat what you like, communicate when and how you like, and feel what you like with total disregard of someone you’re in a relationship, you’ll either end up single or with a shell of who you initially decided to date, and vice versa.

Losing yourself results when compromising becomes significantly disproportionate.

The difference between effectively compromising and changing who you are for someone is compromising takes two participating parties, while losing yourself results when compromising becomes significantly disproportionate.

I truly believe the key to maintaining a healthy degree of compromise within a relationship — without one party being buried by the other — is to find security within yourself, create an environment to communicate around insecurities and criticism, while going into the relationship accepting who your partner is at their core. There is absolutely nothing wrong with growing with a person, but letting someone have the space to grow is just as important as asking them to compromise.

The key to maintaining a healthy degree of compromise within a relationship is to find security within yourself, create an environment to communicate, while going into the relationship accepting who your partner is at their core.

Call me idyllic, I suppose, but this is what I believe is the foundation of a healthy, stable, loving relationship. Nothing is perfect, but it’s about finding someone who you’re willing to live through the imperfections with.

Entry 07 | May 4, 2018

After a few dates me and this guy have decided to carry on with a strictly sexual relationship. With this, we want to set boundaries and have some rules. Are there some less obvious or important boundaries/rules you recommend we instate before beginning?

First and foremost, I commend you for communicating at a level that you’ve come to an agreement on what works best for both of you and that you recognize boundaries are only going to make this a better, more respectful, more fun, fulfilling experience for both of you.

The key is to be open and respectful, but not treat this person like you’re in a romantic, monogamous relationship.

In my eyes, friends with benefits means you are definitely sleeping with or dating other people or are allowed to. If that’s not the case, you might want to reconsider what you’re really doing. That said, you need to determine if you’re going to be the friends with benefits that discusses the other situations in your lives or treat them more as a ‘don’t ask, don’t tell’ thing. While I wouldn’t recommend asking advice on your other joints or trying to create jealousy, transparency works for some people, particularly if those they’re seeing live in different cities. Others though, prefer the out of sight, out of mind/don’t ask, don’t tell approach. Neither are wrong, but both of you need to understand what you’re comfortable with. In my experience, the more infrequently you see each other, the more transparent you can be.

The key is to be open and respectful, but not treat this person like you’re in a romantic, monogamous relationship. Treat them how you treat your friends. You probably shouldn’t hang out every single day, and they shouldn’t be your automatic plus one to any events or parties. Weddings and family functions should be off limits, as should other significant-type of milestones, like meeting the parents.

PDA always leaves things fuzzy; I’d strongly advise against it. Holding hands or kissing in public settings allows others to assume you aren’t available, and you are.

Maintaining your separate lives outside of the time you spend together makes it easier to keep things casual.

Similarly, bringing him or her around your friends can quickly lead to a “what are we doing” situation. I’m not saying you shouldn’t be out in public together, but you don’t need to let your friends be friends with them. Maintaining your separate lives outside of the time you spend together makes it easier to keep things casual.

What you do need to do is make sure to have great communication; always answer their texts, do not treat plans with them like they can always be broken, and don’t hesitate to bring up issues that make you uncomfortable or insecure. Do not treat this person like a last resort. That’s a dickhead with benefits, not a friend with benefits. A common misconception is that you don’t “owe” anyone anything that you aren’t in a relationship with. But, it isn’t even about “owing” anyone anything; it’s about respect and communication. You can be honest with friends with benefits like you would with friends without benefits, your mom, or your significant other.

The best way to seamlessly move forward is to maintain your independence, while respecting the other person’s.

Ultimately, if the communication is clear and honest, these don’t need to be hard fast rules. Whatever feels right to you guys is your business, as long as you are both on the same page. The best way to seamlessly move forward is to maintain your independence, while respecting the other person’s.

Entry 06 | April 20, 2018

Hey Rae,

This dude I work with and I am kind of feeling each other. We don’t work in a traditional environment like at the same company, but we do work together on projects. We had a moment over the weekend, but we were both intoxicated and in front of our co-workers so nothing happened. He lives in L.A. and I live in New York. I think he knows I’m feeling him, but I didn’t personally tell him. I also don’t even know when the next time I’ll be in L.A. We didn’t grab each other’s number but we did follow each other on IG. Should I slide in the DMs? Should I leave it alone?

Before you jump in the DMs, I think it’s important that you figure out what it is you would like to happen with him. Do you want to date long distance or be in a long distance relationship? Do you want to sleep with him and establish something more casual for when you’re both in the same city? Do you just want to text each other and then be weird IRL? Do you want to just see what happens? (I’d recommend to not “just seeing what happens” considering it could affect your money.) Granted, there are other factors, like what he would want, but figuring out what you desire should be your first priority.

Figuring out what you desire should be your first priority.

Working with someone you’re seeing isn’t always easy, particularly outside of an office where you may find yourselves drinking while working and with very little structure. It makes sense to start to slowly get to know each other.

Truthfully, if I were in your shoes, I’d jump in the DMs extremely casually, in a nonsexual way. You cannot get physical literally right now, so why put in that energy? It’s probably better to get to know each other this way rather than trying to play it cool, flirt, get to know him, and keep it on the low in front of people you both work with like last weekend. Don’t fully friend-zone each other and talk about other people you’re dating, but talking about common interests — particularly things outside of your work — can allow you to get to know each other better while figuring out if this human is worth putting your work at risk.

He might suck. He might be great. You won’t really know until you talk to him more in depth.

However, I do still recommend to tread lightly. It’s probably better you don’t have each other’s phone numbers yet. There’s absolutely no reason to expedite anything as you don’t even know when you’ll be able to see each other in real life. Don’t put all your eggs in his basket, but don’t hesitate to get to know a little more about him.

Lurk deep before you slide in.

Patience won’t kill you, and casual DMs won’t kill your work. Find some chill. I think once you figure out the reality of what you want and/or what can happen, you won’t feel like it needs to be definitive as to whether or not to jump in the DMs. You can’t get pregnant off a DM and a DM ain’t a ring on your finger.

Besides, you got the ‘gram. Lurk deep before you slide in. Good luck!

Entry 05 | April 6, 2018

Is it unattractive for a guy to admit that he is intimidated by a woman who (based on her own admissions) is more experienced than he is?

Bottom line: being intimidated by a woman who is more experienced than you is not unattractive. How you communicate it and handle it over a period of time has potential to hit anywhere on a spectrum of being a deal-breaker (for her) to becoming a valuable pleasurable, sexual experience and honest relationship (for you).

Now, ask yourself: is it her confidence that’s intimidating or her experience? Or both? If it’s her confidence, you definitely do not want to approach it like a little bitch … for lack of a better word. However, you definitely don’t want to fake your feelings with an inflated sense of confidence either. And, most of all, you do not want to make her feel like she’s “too much.” (Triggered.) If she’s smart, she’ll realize the reality is you feel like you’re not enough.

You do want to embrace her confidence, and let her know you admire it and appreciate it. Don’t make backhanded statements or try to knock her down a peg. Men that feel threatened by confident women frequently try to make them feel small or belittle them by mocking or dismissing their self-worth to make themselves feel better. Shit is lame.

If it’s her experience, I think it’s probably best to figure out what about it is intimidating. Are you comparing yourself to her past partners? Luckily, if you’re aiming to please her, this should be looked at as a gift, not a curse. When you discuss your likes and dislikes, she’ll actually know and probably be more apt to share than others who are less experienced than you.

If it’s both, let go of every idea about masculinity in the bedroom. Realistically, you need to adjust the way you’re looking at it. Absolutely do not go into this sounding like you feel bad for yourself. Let go of that insecurity, and take advantage of what a great thing this could turn into between you and your partner. It’s OK to let her know you’re intimidated, but with communicating it, you should also take action to figure out how to not be. You don’t need to say it more than once, and it might be better received if you made it less about her being intimidating and more about you having never done certain things before. You’re in a great position.

Ultimately, if you can’t handle it and it’s going be something you bring up constantly, it’s negative. Do yourself a favor: know your limits and stop seeing her. Let someone else value her experience if you see it burying you.

Entry 04 | March 26, 2018

Do you consider sexting (outside of your partner, while in an already “committed relationship”) cheating? Would you bring it up to your partner if you suspected them of doing it?

Yes, I do consider it cheating, and I would not be able to avoid bringing it up if I suspected my significant other was sexting with someone else. Sexting frequently happens between people that haven’t had sex, but can also be a precursor to foreplay or something to maintain in between seeing each other.

It’s hard to know specifically how you should bring it up without having an understanding why you suspect your partner is doing it. Let’s just say you know for a fact they are sexting someone else — whether you saw it or someone showed you screenshots. I think it’s important to figure out what you want to come out of the situation. Do you want to just break up with them? Do you want to know why they were doing it? Is there a chance that it might not be true? You’ll need to be prepared to ask if anything beyond sexting happened. Have they been physically intimate with this person that they have already been textually intimate with?

You need to decide what your deal breakers are and what needs to happen for you to stay.

Ultimately, you need to decide what your deal breakers are and what needs to happen for you to stay. Does the sexting need to stop? (It should need to stop if you’re in a monogamous committed relationship.) You have to figure out what you’re comfortable with in order to move forward in the relationship and then bring it up.

This is definitely a conversation that needs to be handled face to face with little distraction as possible, because, let’s be honest, you might be breaking up. Sexting is an intimate exchange of words and/or photos implying sexual-oriented actions are desired to be made toward or with the sext recipient. Whether they meant what they said or not, your person has allowed someone else to think they want to have sexual contact with them. Realistically, even if you don’t consider sexting as cheating (it is), it’s a violation of trust. Broken trust can very often be the downfall of relationships, particularly if it starts with infidelity. Imagine what every single smile at a phone screen could trigger from staying in a relationship with someone that’s been sexting someone else behind your back.

Even if you don’t consider sexting as cheating, it’s a violation of trust.

Once confronted, if they offer that they didn’t mean what they said, then they were lying to whoever they were sexting thus making them a liar. If they sent provocative photos or nudes, cut them out of your life. Finally, if they don’t consider it cheating or try to sell you that it’s no big deal, then their content of those sexts are amateur-level and you should move on off the strength.

The bottom line is, you don’t need to be committed to someone who is sexting someone else. If they can’t be with you and not sext other people, they should be single and sext as many people as they want.

Entry 03 | March 9, 2018

So, before I get to the question. [Here’s a little] about me:

Aside from some on and off FWBs in college, I didn’t date. I proclaimed how I didn’t have time to put up with foolishness. I had (have) little patience or understanding for my friends’ relationship woes; my only advice [would] be to “break up with him” because I simply didn’t (and don’t) understand putting up with shit from temporary men.

[deep breath]

But, now I’m 22, starting my adult life in the Big Apple and well, it can get a tad cold and a tad quiet all by myself. I have plenty of friends. But, ya know, I want to experience some semblance of romantic love, to get started dating now before I wake up single at 32 with no experience and a ticking biological clock.

I’m a “vibes” type. I need that personal interaction to spark some interest. I hate the apps because I feel zero desire to interact with these flat faces on my screen. (Plus, I’m Black and, statistically, those apps are not meant for women like me.)

Any tips on how to date in the city or make myself attractive/approachable to men? My friends love me too much and their only advice is to “be myself.” (And if I hear another “love happens when you’re not looking for it,” I will lose it.)

— Single and Ready to Mingle

Well, Single and Ready to Mingle, I am not a “love happens when you’re not looking for it” head ass, and I very much identify with not putting up with shit from temporary men, however, there is a lot to learn about yourself and dating from temporary men. I definitely do not recommend putting up with shit from them, but I think approaching dating more as getting to know new men that you have an attraction to rather than being on the hunt for a relationship will put less pressure on situations to materialize into something.

Particularly in New York, it’s easy to want to just make time for your friends and your schedule. A girlfriend of mine and I were sitting at our favorite bar and she was feeling so fed up with the app and swipe life she expressed she’d cancel any Tinder date to sit at the bar together in a heartbeat. So, if you are not the app type, don’t bother trying to turn into that, no matter how many times people tell you everyone is doing it.

That said, finding people you’re interested in online does not need to be on dating apps. Following someone (and getting the mutual follow back) on Twitter or Instagram that you may be interested in allows you to slowly see what they are into and how they portray themselves. It also offers easy entry points for conversation. Instagram stories or tweets you identify with can simply be responded to without feeling creepy or like you’re making a major move. An ongoing conversation can easily evolve from there.  

Actively invest in knowing yourself, what you like and don’t like, and don’t feel like you have to sit back and wait on a man to show interest in you.

Also, I’d recommend considering approaching men yourself. It concerned me that you want to know how to be more attractive and approachable to men, because, like your friends said, I’d also say to just worry about being your truest self and you’ll attract someone that digs that. Actively invest in knowing yourself, what you like and don’t like, and don’t feel like you have to sit back and wait on a man to show interest in you. There’s nothing wrong with asking someone to grab lunch or a drink if you want to try to get to know them better.

Miraculously, looking back, I’ve met a few guys I’ve been involved with in New York at some random places offline and not out partying. If you are really not into anything online, I met one guy at this panel discussion he was moderating, another worked out of a coworking space I would work out of sometimes, and I met another guy at this screening for a short film he was a part of, but later asked for his number when he was out for drinks with mutual friends. I know New York-based friends that have met men they’ve dated at both going away parties or birthday parties, which usually ends up being a collection of someone’s friends that don’t all necessarily know each other.

Dating in the New York is not easy. The longer you’re here, the smaller the city gets.

I’m going to keep it one hundred with you, dating in the New York is not easy. The longer you’re here, the smaller the city gets, and the lifestyle allows for people to grow in their career without really normalizing any semblance of growing up like you would outside the city (i.e. buying property, having a big wedding, having kids). I think your stance of not taking bullshit from temporary men will benefit you, but I’d encourage you to have a little fun, be proactive about meeting new men, and even be open to long-distance relationships.

Entry 02 | February 23, 2018

Q: My boyfriend isn’t the romantic, affectionate type. He doesn’t say that he’s opposed to it or doesn’t like it. He says he’s just not used to it. Me, on the other hand, I am very affectionate. I love romance. I love to give and receive it. How do you think I should go about talking to him about it? We briefly mentioned it, but I didn’t know how to go about it so I just dropped it. What are some of your tips to have an effective conversation about this? I’d like us to reach a common ground. I definitely don’t want him to think I’m nagging or trying to change him, but it is something that means a lot to me. I know he loves me so it’s not really like I need it to validate our relationship, BUT it would be very nice.

I think the most valuable thing you have going for you here is that he isn’t opposed to it and hasn’t said he dislikes romantic affection. However, as it is something you want, I think it’s important to go into this with patience and expecting to compromise.

If it’s spontaneous romantic acts you’re looking to receive, you should probably not hold your breath for I think physical affection is not something you should live without, particularly if it’s important to you. It will come off as nagging if you are looking for flowers for no reason and surprise weekend trips from someone that doesn’t inherently operate so thoughtfully and giving, but I think people (men, specifically) can learn to give and receive physical affection even if they’ve never been the type.

That said, I also think this is much less of a formal “let’s sit down and have a talk” type of thing at first, rather than something you’ll want address over time as situations and opportunities arise. Most importantly, your actions and your words in reaction to his actions will guide the conversation. I think verbal affirmation of the things you’re looking for on the rare occasion he does them is a great place to start. By pointing out and praising the desired actions, it will hopefully turn into something he will want to replicate with you. Using statements like, “I like when you…,” “It makes me feel good when you…,” or “I appreciate it so much when you …” will affirm the natural (albeit rare) romantic or affectionate actions.

If they are so rare that these opportunities to give affirming feedback are few and far between, try offering the affection you’re looking for and pointing out how good it feels to be able to give that to him. If you’re a naturally very affectionate person, as you mentioned, you won’t need to do it all the time, but try to remember to say things to point out how happy you are to be able to do it with him. Although it may seem obvious, it will be verbalizing what you’re already feeling. “I like to be able to do this for you,” or “I’m glad that you’re the one I get to give this to” can show your appreciation for him and how much you like to be engaged in these things with him without coming off condescending or pushing him outside of his comfort zone with statements like, “See how I do this” or “I wish you did this for me like I do for you.”

I think after you try this, it could be very worthwhile to have a conversation about it by acknowledging what it is your looking for using examples of things you appreciated that he’s done and how it has made you feel.  

Entry 01 | February 9, 2018

Q: A couple months before I moved to a different state in December, I met a great guy after breaking up with the man I thought I’d marry. Obviously, I took things very slow as it was my first time “dating” in my adult life after a long-term relationship. We saw each other at home over the holidays (our parents are from neighboring hometowns), and I just got back from my first weekend visit.

The weekend went well until the day I was leaving when we started talking about the future. Long story short, he says since it would have to be him who moves in the next year or so to make this work, he’s not sure he could commit to that.

Either way, I don’t know when I’m going to see him again. I bought tickets in December to this festival where he lives that takes place in March because he always talked about going. I didn’t tell him about it, because I wasn’t sure what was going to happen when I moved. So either way, I have these tickets. We haven’t officially broke it off, but I’m not totally optimistic, so I was just going to give them to him. How should I say that?

Although you haven’t officially ended it, it seems you’ve made your decision on what’s going to happen which is half the battle. Leaving your fate in someone else’s hands is where a lot of us get it wrong. If you are dead set on giving the tickets to him, I recommend utilizing a “less is more” approach.

Leaving your fate in someone else’s hands is where a lot of us get it wrong.

Where offering them with a multiple choice of options for your not-boyfriend to choose from may seem the simplest and most efficient way to get his answer, we all know that titleless other halves look at this type of thorough communication as an ultimatum. Whether it’s via text or over the phone (because let’s be honest, if you know it isn’t going anywhere and you had this talk IRL, a text will suffice), I think you should go with direct, to the point, and nice rather than the multiple choice question.

Craigslist is less the hassle than trying to communicate with a man about where and when the demise of the relationship will come.

Instead of saying, “I bought these for you want me to join you or not?,” I’d go with, “I bought these for you because I knew you’d like them.” Because you are so clear headed on the reality of the relationship and where it’s headed, I think it’s worthwhile to simply just offer them without desire to use the tickets as test to where he stands on the relationship. You already had that discussion. Believe him. If he changes his mind, that’s an entirely other discussion. He might ask if you are going to come, then it’s on you to choose whether or not you want to prolong the relationship another travel weekend only to have another Sunday night conversation about what you two are doing.

… or

Sell them on Craigslist. Craigslist is less the hassle than trying to communicate with a man about where and when the demise of the relationship will come.


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