Survey the District: My Friend and I Want the Same Guy

Dear Date the District,

So I had a friend from out of town visit, she met one of my best guy friends, and they actually ended up hooking up one night drunk at a bar (all they did was kiss, and just on the dancefloor).  She left town the next day, and other than maybe a couple facebook messages back and forth the week after the hookup, that's all the communication they had.  She then returned to town a few months later, hoping to see this guy.  However, this guy was not interested in her because he told me so (and told me to keep her away from him so that kind of situation didn't happen again).  They both got drunk though and initiated another makeout at the bar (him actually trying to stop her, but her being forceful about kissing him) but that's it again.  This time, they didn't talk at all after she left town, as well as him saying he can't believe that he madeout with her again.  Fast forward a couple weeks later, and me and my guy friend are just hanging out on the weekend like we always do, but this time (we're both drunk) we started holding hands at the party, and ended up kissing (I asked him hold my hand that so this sketchy guy would stop hitting on me, but the kiss just happened).  He then asked me if I wanted to go back to his place, but I told him that it would be awkward and I went home myself.  Although we both do agree that it was bound to happen, there's definitely been some tension for some time.  For the rest of the week, we thought the situation that night was funny, and all of our friends thought it was cute.  We act as if nothing has changed.  The very next weekend, though, we ended up having sleepovers both Friday and Saturday nights, and got dinner and brunch double-date style with another couple (I paid my own share though, since the other couple was also splitting).  And now it's to the point where we talk even more than we used to, so it's literally all day over gchat and all that.  So at this point, I realize I may like him as more than just a friend, but am not 100% sure yet if I want to date him, but I could see it happening.  So my question is (remember, this is still at the point where I'm not sure what will happen, and I'm not expecting anything) if something DOES happen in the future, how should I tell my friend (who actually is interested in him) about it?  She's from out of town and doesn't visit that much at all, and they don't keep in touch or anything.  In fact, whenever she comes up, my friend always says he can't believe he made out with her another time.

OK, so maybe we could have edited down this intro.

The most important thing is, your friend got there first (and the fact that he kept telling you that he can’t believe he made out with her is, frankly, probably not something you should be harping on so much if she’s a good friend).

If you exist, you’ve probably been in at least one situation where you and a friend both like the same guy.

And it almost always comes down to one decision: who’s more important to you—the girl, or the guy?

In this situation, it sounds like the guy is a close friend and the girl is just a friend, so maybe it’s a pretty easy decision.

We know about a million bumper stickers and back-in-the-day AIM profiles would encourage you to put chicks before dicks, but anatomy has nothing to do with it. While putting speculative love interests before friends is probably going to make you lose more than you gain, most 20-somethings have more acquaintances than they know what to do with (for proof, look no further than the name game).

With close friends, it’s different—if you think about it, every romantic relationship in your life except one (or maybe two or three) is bound to fail, so why ruin a friendship when there’s a pretty good chance this guy isn’t the one?

And if this girl were just a friend and the guy were just her ex-boyfriend that you’d only met a few times, it’s also probably not worth the risk. In general, girls are far less likely to forgive and forget, and you’re basically gambling away a friendship that won’t be there to support you if (but probably when) things don’t work out.

But when you know the guy, and you’ve developed a friendship, and you have a sense of what kind of person he is/what kind of boyfriend he’d be, it’s a different story. The problem is, it’s probably much easier to overvalue your friendship with the guy (and downplay your relationship with the girl) when you’re excited about someone new.

You really need to think about this objectively (and probably enlist the help of a close friend with first-hand knowledge of your relationships with both parties). But the if girl’s more of a wall-post buddy and the guy’s on your speed dial, the potential payoff might be worth the risk.

Still, if you are going to go for it, you need to accept the fact that there’s a good chance this friendship is over. It’s less about your girl friend being selfish and more about the humiliation of being rejected by a guy and then having him choose the friend you confided in.

If she doesn’t care, great, but you need to be prepared for the worst-case scenario and not resent her for it/talk shit about her behind her back.

That doesn’t mean you should disregard her feelings when you tell her. Wait until there is actually something to tell her (no sense confessing in a few makeouts if you both decide it’s not going to work out a few weeks later). But if you start dating, she deserves to be the first to know, and you owe her a phone call/in-person explanation.

Say something like, “Look, I’m in a really shitty position right now, and I wanted you to hear it from me first. John and I realized we both have feelings for each other, and we’re going to start dating. I don’t really know what to say, except that I’m really sorry—I know you guys had a thing, and trust me when I say that I wouldn’t do this to you unless I really thought John was the one.”

Do not mention the fact that he regretted making out with her. Don’t reassure her that he didn’t like her anyway. Don’t excuse your behavior or put her down in any way—just apologize. Grovel. Do whatever you can to make her feel better.

Don’t let on that you had inside information on the situation from both ends—don’t say anything like, “John feels awful too—he just didn’t want to get involved with someone from out of town.” She’ll feel even shittier if she knows you both talked about their fling. Don’t ask John to get involved either (i.e., Facebook message blaming it on the out-of-town thing). This is between you and her, and if you want to salvage your relationship, you need to keep it that way.

Yes, it’s a hard convo, and yes, it’s a little bit awkward, but it’s really the best course of action in a shitty situation. If she hears about it from someone else first, or, even worse, if she sees something on Facebook, she’s going to feel even worse.

There’s a flip side to this. You may find yourself the friend in this scenario sometime in the future. Remember how shitty you felt about this, and remember that it wasn’t about her, and maybe you can find it in yourself not to hold a grudge—or, at the very least, not to forward those incriminating photos to her would-be boyfriend.