Dunno if this is "worst date ever" but it's a pretty big fail from my perspective and a pretty good summary of the failures in my relationships. I think that if I'd been the guy in High Fidelity something like this would be the story I'd tell at the beginning to frame the others.

Was uhh 23 maybe older I forget, in college, I took a girl to the opera on a date since (a) the IU music school is awesome (b) if you're a student then for $10 you can see an opera with people who in a couple years you'll have to pay $150 to see sing in Chicago or wherever the fuck (c) I like opera so if the date is a fail then I'll still have a good time (d) everyone knows cool guys take girls to the opera on dates and that's how I'm going to stand out over all the frat guys in college. B)

So the production is amazing and in spite of saying maybe 10 words to each other all night she wants to go back to her dorm room to "get food". Sweet, it's on. We get back there and after about 10 or 15 painfully awkward minutes of sitting on her bed talking about whatever and watching her eat a clif bar I finally sack the fuck up and do something, I don't remember exactly what, but we're making out and feeling each other up and it's on like donkey kong when I realize I didn't bring any condoms because in spite of all my internal hyping I didn't really think there was any way a dorky guy like me would actually have sex with a gorgeous girl like her. And plus it was like our first or second 'date' so there's just no way right, I mean come on, you have to put in more 'work' than that because... I dunno. But I know that if I admit that to her, then the smooth persona that I had so artfully maintained (or so I told myself) - which was the whole reason she gave me the time of day anyway, obviously - would pop like a balloon and she'd LOL in my face and throw me out. So I'm paralyzed, and wind up going to sleep in her twin bed in my underwear (tighty whities except black B) with what is probably a very confused and disappointed woman.

She never returned my calls after that, obviously. I still wonder if it was because she was pissed that I wasted her whole night and didn't want to give me another shot at wasting her time or because she had similar neurotic thoughts and didn't want to face me after being 'rejected' or something.

Pretty funny to think about how many 'rejections' I might have had that were actually motivated by similar wacky stuff that someone was too embarrassed to admit.

Good thread