A few weeks ago, my close guy friend and I hooked up under very drunken conditions (it was St. Pat’s, sue me). Now we’ve started hooking up on a regular basis and it seems like it might go in a dating direction. He’s nice and sincere and nerdy and considerate and awesome, I mean I’m friends with him for a reason. On top of that, the sex is fun and great. BUT, in the harsh light of day, I just don’t know if I think he’s that attractive. My shallow self thinks I can do better, that I’m cuter than him, etc.

Should I get over my vain self or was it doomed from the start?

Both.

You should definitely get over yourself, but you don’t strike me as the type who’s capable of rising above petty vanity, which is precisely why this shit is doomed in the first place. (I can tell these things. Sue me.)

Go ahead and do your thing for a while. Might as well, ‘cause this ain’t gonna have a happy ending. Now that he’s been elevated to fuck buddy status, he’s not gonna go gently back into the friend zone.

Eventually, you’ll get bored and start acting distant, but since you guys were already close, things will just get sticky and confusing. Eventually, you’ll fuck some random hot guy just to shake things up, and it’ll destroy all trace of your former friendship.

Oh well. Too bad life isn’t a romantic comedy.