What to do When You’re in Love With Your Best Friend

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Call Your Boyfriend

Ryan O’Connell is a New York-based writer. He likes shoegaze, the Olsen Twins, and figuring out why people do the things they do. Oh, and he tweets. Check back each Thursday for his latest Call Your Boyfriend column. (You KNOW you have a question. Send it to Ryan.)

I need some clarification re: dating your friends.  I know that in theory, it’s probably not a good idea. But when it comes down to it, WHY NOT??  I recently (drunkenly) came clean to my best friend and told him that I have feelings for him.  He took it well and explained that he didn’t feel similarly, and then we made a promise not to be weird around each other –something I shouldn’t have said because I definitely can’t promise that.

We went to college together and ever since we met, I’ve gone through varying degrees of liking him.  On the one hand, he is my closest friend and we definitely rely on each other for emotional support.  On the other hand, he has a tendency to make out with me when we’re out and about with our friends.  I’m not the only one he’s done this with, but for some reason I’m turning sentimental and really taking these inebriated hook-ups personally.

I feel like I want him to take accountability for leading me here, because I was really starting to (wrongfully) think that the feelings were mutual.  When sober, we obviously enjoy each other’s company and have what I thought was a fairly flirty rapport.  All of this is sensitive for me to communicate to him because we’ve NEVER actually talked about any of our drunken physical escapades after they’ve happened.  Is this news to him??  So now my feelings are hurt, he’s tip-toeing around me, and I just want to know how I ever ended up here??  I’m so confused.

You ended up here because you are human and need to be loveeddddd, just like everybody else does! Okay, sorry for quoting The Smiths. I really don’t mean to kid because your situation sounds like an all-too-common bummer. It makes me really think that life would just be 100% easier if we could choose whom we were attracted to. Imagine if our mating ritual required feelings that were completely reciprocated. I’d be getting a lot less questions like this one, let me tell you.

I can understand why you feel confused about your best friend not being into you, considering he likes to stick his tongue down your throat whenever he’s wasted. That is a TAD misleading, isn’t? I mean, I’m all for a wasted meaningless makeout, but not when it’s with my best friend. There’s no such thing as “meaningless” when a sexual act is done to someone who is important to you.  Shame on your friend for being so careless with your feelings! His mouth wrote a check that his heart couldn’t cash!

Everyone has different boundaries and concepts of what’s right and wrong. Your best friend probably didn’t think anything about your makeouts other than “HEY GIRL HEY I’M DRUNK SPRING BREAK FOREVER!”

There’s an important lesson to be learned here, though, which is that people won’t always treat your feelings with kid gloves. Everyone has different boundaries and concepts of what’s right and wrong. Your best friend probably didn’t think anything about your makeouts other than “HEY GIRL HEY I’M DRUNK SPRING BREAK FOREVER!” I’m also going to give him the benefit of the doubt and assume that he didn’t know that you had feelings for him, although who knows if that’s actually true? The point is that when it comes to love and relationships, there’s always going to be the person who’s reading into every kiss, every text message, every gesture, while the other person is just YOLOing it up and having fun. I’m always the former. I’m always the person suffering from analysis paralysis. Meanwhile, the object of my affection just seems to be floating through life, not giving his actions towards me a second thought.

How you proceed with your best friend is entirely up to you. Can you deal with being close, even though you now know for certain he’s not into you? Some people can do this. Some people can swallow it all down and still be BFF. I’m not one of them. If I know a person I like is not into me, I GTFO because it’s too painful. But I’m also a raw nerve, and immature and selfish. Other people are far more evolved and have the ability to separate their feelings. Perhaps you are one of them? In the end, choose the option that causes the least pain. That’s usually an indicator that you’ve made the right choice. And if you feel like you need to call him out for potentially leading you on, then do it. If you decide to remain friends without vocalizing your feelings, you’re basically a train crash waiting to happen.


I like to get choked during sex. Is that weird?


Unless you’re having sex with an animal, your brother, or a five-year-old, nothing is weird.


Hey Ryan,

I’m a second year college student who before college had never had much experience with guys (read: none). I was shy and overweight, and probably the most haphazard dresser ever. But now I’m getting noticed, which is great, but the couple of guys that have actually made moves, made out with me and just kinda…fizzled out. I don’t know if it’s because I quite bluntly said I wasn’t ready to have sex? They hung around and texted and stuff, and I WAS interested, and would have slept with them at some point, just…a little later on. They both eventually said that it was probably not the best idea for us to be together. I’m a stickler for the whole trust-before-sex thing, but at 21 is it a turn off?

Ever unsure.


Okay, so are you ready for a truth bomb? Yes, you’re right. Those dudes might have bailed because you didn’t want to bone ASAP. I know, I know, people are gross and shallow and scaredy-cats, but that’s just the way it is sometimes. They’re not all like that. The reality is that everyone has things that are considered “dealbreakers.” Nowadays, people have such bad dating ADD that it’s like they’re just looking for an excuse to abandon ship.

The reality is that everyone has things that are considered “dealbreakers.” Nowadays, people have such bad dating ADD that it’s like they’re just looking for an excuse to abandon ship.

That being said, there is NOTHING wrong with you not wanting to throw a penis-and-vagina party right out of the gate. You’re a virgin. I get it. You want things to be medium special or, at the very least, you don’t want to lose it to a random. You’re entitled to that. Don’t let anyone take that away from you or make you feel bad about your convictions. If waiting a little bit to have sex is enough to send someone screaming, screw ‘em. (Well, in your case, don’t screw ’em.)  At the end of the day, all we really have are our convictions. Whenever you start dating someone new, there are compromises to be made, which is fine. Part of the beauty of relationships is learning how to be less centered on your needs. However, there are certain things you should never budge on, regardless of any pressure you’re feeling from an outside party. How you lose your virginity is a good example of this, but other examples could be your feelings re: religion and politics. A friend’s mother once told me (on a high school field trip to Medieval Times, no less) that before you get into an LTR with someone, you need to see eye-to-eye on three things: sex, religion, and politics. Doesn’t that make sense?

Stay true to who you are and don’t ever feel like you’re giving up too much, because that will just end in resentment and be the undoing of a relationship. Be a proud virgin! You’ll eventually find someone who won’t mind waiting for more than 2.5 seconds, and then you’ll finally have sex, and everything will be A-OK.



I have a dilemma. I’m a 38 year old woman who hasn’t had a lot of dating experience in the last 15 years (a family death and a bad break-up contributing). According to a most people I’ve met, I look a lot younger than 38 — I’ve been quoted at 25-30. I’ve recently started a new career, and as I’m at the bottom, I’m surrounded by guys around 25 and up. I find myself so attracted to them, and I wonder if I need to be worried that I’m so far out of what would be considered a “typical” age range. I recently met a guy who is, probably, around 28-29, and I just had the best time talking and flirting with him. It was as though we had known each other for ages. But I assumed he was a lot younger than me, and I was hesitant to show my attraction. I don’t think I’m  emotionally immature, but I worry that there might be something wrong with me for being attracted to, and wanting to date, a 29 -year-old. I don’t even think about age when I’m attracted to someone, but once I realize how old they are, I feel like a cougar. Am I hopeless?

Hey Cougar,

Please. Older guys date women who are barely out of high school and are celebrated for it, but if a woman dates a younger man (Ashton + Demi?), she’s seen as a cougar? No. We need to retire that inoffensive term. Your insecurities just stem from society’s harmful attitudes about women. Put down the Us Weekly and have sex with whoever you want! Just be aware that a 28-year-old dude might not be on the same “journey” you are. Trust me. I’m 27 and I can tell you with confidence that a lot of them aren’t fully cooked yet.

Check back each Thursday for Ryan’s latest Call Your Boyfriend column. And you KNOW you have questions — send them to Ryan.