If you’re a dude loving (although the same rules essentially apply if you have sex with your best girl friend––though for better advice, I highly suggest you check out Riese’s amazing site, Autostraddle) girl, there may come a time when you become best friends with an extremely attractive boy, who may have taken up permanent residence in your emotional headspace.

It may just so happen that you may end up in a situation (alcohol induced or otherwise) where it becomes absolutely neccessary to kiss said hot, sweet, amazing unicorn-dude who just so happens to be your best guy friend. The next thing you know the clothes are flying, the saliva is exchanging, and you and your guy friend are boning. Like ridiculous, straight up boning.

It might be tender and romantic, and a total Dawson and Joey moment which only serves to underscore the years of unspoken sexual tension between the two of you, or he might just blow a raspberry on your face mid-tender moment. Either way, you, foxy lady, have just had sex with a great guy friend, and if you’re right here, reading this post, you’re probably wondering what the hell you’re going to do about that. 

First off, resist the urge to emotionally purge. Don’t do the post sex “what does this all mean” conversation until you know precisely how you feel. A drunken romp may just be that––a drunken romp, or it might be the catalyst for something deeper.

What are his reactions in the morning? What are yours? If it’s back to fart jokes and high fives, you might have to think long and hard about this one. Though it’s too soon to tell. That being said, if he makes you your favourite breakfast, and brings you your favourite coffee (or remembers that you only drink green tea in the morning), chances are you can safely move to the next step.

Okay, maybe not just yet. It might be best to get a sober second opinion. Find your most Oprah-esque friend (aka the girl who should be charging for her life advice), a therapist, or even your mother (god forbid), and ask them “what does it alll meeeeeeean?” Make with the whining, and the hashing out of the details…it’ll make you feel better, and you may arm yourself with a pragmatic plan of attack. You probably won’t find the answer you’re looking for in a repeat viewing of Nora Ephron’s “When Harry Met Sally”––which will only serve to heighten your expectations––nor will you find them at the bottom of a Yahoo Answers thread.

If you’re sure that your feelings are pointing you in the direction of “TELL HIM HOW YOU FEEL, ALREADY GODDAMMIT WOMAN” (note: most likely the case if you’ve already been hit by the feelings bus), then you can definitely move on to the next phase of operation deep-and-meaningful. If you’re not sure how you feel: Let it simmer down for a month, and then check in to see where you’re at.

If you’re planning to TELL HIM ALREADY, here’s a way to do it that doesn’t come off as creepy, desperate, or a tad neurotic (even though you may feel like you’re all of the above at this stage). Invite him out for coffee or lunch…or even just a long aimless walk, and say something along these lines (add your own personal flair if you want).

YOU: Gee, [name of dude here], I’ve been thinking a lot about that time we had sex. How have you been feeling about it?

Wait for an answer. If it’s in the positive such as “I can’t stop thinking about it”, “Can we do it again”, “Actually I’ve been secretly in love with you for YEARS and finally worked up the courage to stick it inside your sexy lady gullet, and would love to make you breakfast and get a dog with you, and watch all those television shows that you love with you because YOU COMPLETE ME”–then by all means, continue on with that conversation, and continue having the sex. If it’s something along the lines of a resounding “Meh!”, or “I haven’t thinking about it”, or even “I was trying to get over my ex,”, or even better–– “We had sex?”, it’s probably time to abort mission.

When having sex with a friend, the temptation is to continue having sex with said friend––because the connection is already there, and it’s easier than going out and finding a whole new partner. It’s familiar, it’s comfortable; it’s the a huge down filled comforter of sexy time. You’ve pretty much hit the jack pot if you have a close friend that you can fuck––until it becomes complicated. Which it can.

But it doesn’t have to be. Just use your words, kiddies.

Or, I mean, you can passive aggressively link them to this article. Either way, you get the point across.

~ Anonymous