Ask Him: Oops, I’ve Been Having Sex with My BFF


Q: “After more than a decade of knowing each other, I recently had sex with my best friend. Then, a few days later I had sex with my best friend again. Last night made it the third time, but we haven’t really talked about it at all. I know we’re going to have to discuss it at some point, but I don’t know how I should go about it. What should I do? Am I making a mistake?”

A: People seem to have adopted this perception that having sex with your best friend is a terrible thing. But I don’t necessarily buy that. Many of the most successful and beautiful romantic relationships begin with close friendship. You know, someone said that love is friendship on fire, or something like that, and it worked out for Harry and Sally and Jim and Pam. Also, my mom tells me often that I will end up with one of my best female friends. (She tells me to ask girls out who I’m friends with based on the quality of their Tweets.) And she knows things about life and love. I think.

Of course, sometimes giving your best friend a shot at the sex title can be a mistake, but it’s fairly obvious when it is. Like, you might not really be attracted to your friend, but you get hammered some night and maybe you’re lonely and maybe it’s been a while and sometimes it just feels good when someone listens to your problems and cares about you, so you let him toss you one, despite your knowing that you would never want to be with this person in the long term. It becomes a mistake when only one of you wants more than a one-off bang, because then that person is sometimes unable to go back to being “just friends.” And then you’re out one of your best friends, which sucks. They don’t restock so easy.

But obviously that doesn’t seem like the case for you, since you’ve gone back for a second and third helping. (I’ll have some of what that dude is bringing. He must know what’s up.)

I agree that at some point you’re going to have to talk about this sex stuff, but if both of you are kind of going with it and it feels good, I don’t see a reason to rush it. People always want to talk about everything, but when something is fun it’s not always crucial to dissect it and pick it apart. This isn’t high school, I hope, and you don’t need to make a decision re: what should happen next. What I’m saying is if you enjoy f**king your best friend, why risk potentially f**king up your enjoyment until your hand is forced? You never know, this might just seamlessly transition into a serious relationship without the two of you discussing it until you’re well into the exclusive, almost in love phase. That’d be a nice story for the kids: “Well, your father and I were really good friends. Then I had sex with him once, then again and again, and we kept doing it. Then we moved in together. Then one day he was just like, ‘Want to get married?’ And I was like, ‘Yes. Yes I do.’”

If possible, you should take some time during this “we’re having sex but not talking about it” phase to consider your feelings toward your friend and how they have changed since things became sexual. You don’t want a knee-jerk reaction if he brings up the topic of what in the hell is going on and what might happen next. Just because you’re not talking about it doesn’t mean you shouldn’t be considering the implications of starting or not starting a more serious relationship, or the implications of attempting to maintain a “friends with benefits” arrangement. Maybe even prepare a PowerPoint presentation. This is your best friend we’re talking about, here. The way this shakes out is ultimately going to have an effect on your life that is bigger and more important than if you were to navigate the waters of the sex and wooing process with someone you recently met at a bar or online or wherever.

OH, and final thing: try not to get knocked up. That’ll make for a very strange situation, one that is a good plot for a movie but not one you want to introduce to your personal life.

Best of luck. At the very least, I hope the two of you are able to stay best friends.

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