I fail at dating

This may be a shock for you all, but I am not the world's leading expert on dating and/or relationships. I know, everyone out there is really surprised! You're all like, "What?! How can this be?! I thought Petey was totally the most informed person when it comes to romance!"

I'm very sorry to disappoint you all.

My college is having an annual pride prom this Thursday, and I'm a little bit nervous, as I don't yet have an actual date. I would love to have a date, but as I can sometimes be a little bit awkward, I'm not entirely sure that this is going to happen.

I can imagine a lot of scenarios in which I'm an extreme stud and win my potential date over in a matter of seconds, sweeping him/her/zir off their feet on a wave of charm, romance, and handsomeness. Unfortunately, my interactions with persons of interest usually play out something like this:

Me: Hey.

Romantic interest: Hey. What's up?

Me: Not much. How about you?

Romantic interest: Same.

Me: So...um...

Romantic interest: (silence)

Me (inside head): Just ask! DO IT, YOU COWARD!
Me (out loud): Um...well...I gotta go to class...bye.

That is the level of my skills.

My natural tendency to make a disaster out of any situation, my complete social awkwardness, and my social standing as the King of All Nerds combine against me in situations involving dates and/or romance.

Granted, I've hit it off with a few people who thought my nerdiness was cute or that I was mildly entertaining.

I'm considering finding someone to pose as a date, but this seems a little too Pretty Woman-ish, and I also think it might serve to lower my self-confidence if I have to get someone to pretend to like me for an evening. And I'm poor, so I probably couldn't afford to put this plan into action, anyway. And who would I be pretending for, anyway? I know my school's entire LGBT community and they all know I'm a weird single tranny. Most of them know me intimately enough to realize that if I show up at pride prom with a random person, I'm just pretending.

Conclusion: find the nearest gay man and dance!