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

Entry 19 | November 30, 2018

I met this guy at my job, a coworker. 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 PhD 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 of 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 timeframe 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 re-learn 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 re-learn 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 break-up 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 headspace 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 backstory 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 break down 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 bottomline 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 break-ups, 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 can not 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 themself 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 are kinda 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 non-sexual 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 dealbreaker (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 towards 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 bottomline 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 co-working 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 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.


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.