One night last year one of my friends, who I have always thought is really hot and for whom I'd always had a bit of a thing, asked me to sleep with her and I turned her down.

This friend and I had an up and down history. We went through a period where we were like best pals, hanging out and drinking beers every day, then we went through a period where we could hardly stand to stay in the same room with each other unless absolutely forced to do so. On the night of the potential tryst, the idea of which I admit to fantasizing about on a number of prior occasions, we were most of the way out of a hating each other period and getting back to being good pals again.

Four days previously, I had just started dating another girl.

The whole night was entertaining and somewhat surprising. I met our friends out at a bar (sans girlfriend) wearing one of the ugliest shirts I own, a baby blue Philippino tuxedo shirt with these embroidered braid patterns running horizontally across the chest and buttons all over the place (I think I counted them once and came up with 18 buttons strategically placed a different locations on the shirt). I also had on khaki shorts and my six-year old Birkenstocks. Suffice it to say that I probably was not at my most attractive, so getting propositioned for booty was not on the list of expectations for the evening.

I didn't really expect to spend much time out drinking that night, but as the evening progressed, things just keep getting more and more interesting. At one point one of my other friends decided she needed to spend some time displaying her bra and thong to me and another buddy of mine and then acting all embarrassed about doing so before doing it again five minutes later. Later that night this other girl who looked like a doped up skater version of Lucy Liu came over and starting dancing with the wall next to where a few guys and I were shooting down Newcastle and Bud Light. I think she was trying to dance like a clubgoer on Ecstasy with those glow lights or something, but in the end she really looked she was a little out of practice on her Tae Bo videos. Not good times. So we laughed and danced around with her for a while and somehow kept unintentionally bumping her into one of the stools surrounding the table next to her. By the way, alcohol in no way influenced any of these events.

Anyway, as the night grew a little late, my hot friend, with whom I had been talking on and off all night, comes up to me and says that she needs to ask me something but that she's not going to because she can't. Rrrright. So I start pressing her to just ask me, because it's obvious that she wants to, but she keeps rebuffing my requests and disappearing with her drink to consult with her underwear-flashing friend about something or other. When she returned, we went through this little routine a few times more, until I finally said, "look, just ask me, because you're not going to be happy with yourself unless you do, and honestly, you know me. I'm not going to freak out about whatever it is. No big deal." So she finally pulls me aside and pauses before starting her inquiry.

"I already know the answer to this but I want to ask you because I'm drunk and I don't know. Come home and have sex with me tonight."


I try not to let my eyes grow too large, and I am on the cusp of starting my answer when she cuts me off.

"I have to ask you because I know you care about me and it will be fine and it will be good and I cannot do that with any of these other guys because it will just be sex with them and even though it will be nothing more than that for us I know that I'll be safe with you and that it won't be this cheap thing for you and that it will be comfortable and that you care about me and that it will be fine and you won't think differently of me because of this and I'm really horny and I just need to have sex and I know you're already going to say no, so it's fine."


Timing has never been a friend of mine.

I pause a second before I begin my response.

"Lindsay (this clearly is not her real name), honestly, you know if the circumstances were at all different, if this had happened a week ago, I would be giddily running out the door with you right now. But for as much as I want to, and I really would like to, I can't. It's not right."

I had already told her about the fact that I had a new girlfriend that night, and she was excited about it.

"I know, and I asked you because I knew you'd say no. I'm such a horrible person."

"No, you're not. It's completely fine and I'm flattered, and I'm glad you know I would take care of you and you would feel comfortable with me. But I couldn't cheat on anybody, whether I'd been with them for years or hours."

"I swear I wouldn't say anything. She'd never have to know."

This surprised me a little bit, but I stayed level.

"It's not an issue of her finding out. It's me. I just couldn't do that to anyone."

"I know. You're such a nice guy like that. She's lucky to have you. I'm such a horrible person for even thinking that. [looking at her drink] See what you made me do? Why do you make me like this?"

"Heidi (also not her real name), it's totally fine. I really wish you had done this a week ago, because I totally would have done it. But things are different now and I can't."

Anyway, the conversation continued like this for a little while longer, and then I went home to my apartment and crawled into bed alone, wondering, shaking my head that someone with whom I'd wanted to go to bed for years had just given me an open invite without me even having to take a chance on anything, and I had just turned her down without a second thought. And I truly did it without thinking about it. Physically, of course I wanted to sleep with her, but I had a girlfriend, and though my relationship with her had barely begun, it still was not something I could do. I slowly drifted off to sleep that night with the irony of life fresh in my mind.

I won't say I'm glad it happened, because I know now that I for sure passed up a night of what I wager would have been a really romp in the hay (you ever look at someone and just know that they would be a great lay? This girl is one of those people). And since that night, I've never gotten the chance to request a rain check (which, given the wonderfulness of my current relationship, is completely fine with me). But it is a fun story, and one of those moments to which I can turn when I feel like I'm not really the nice guy I sometimes flatter myself in thinking I am.