Animation by Sam Liacos.

Friend with Benefits is ILY’s newly launched 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 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.