How do I get active in dating? I'm 27 and I'm about

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How do I get active in dating?

I'm 27 and I'm about to start my second semester of grad school. I dated a couple weirdos in undergrad, but not to the extent that I got any real experience. From the 3rd grade through my undergrad, I would get these obsessive crushes on girls. I've finally matured past that, but it hindered me for all those years.

I can be really awkward. As a kid I was diagnosed PDD-NOS, which back then basically meant I didn't fit the criteria for Asperger's, but doctors knew there was something weird about me. Since then I've only been diagnosed ADHD, and I don't know if something's really wrong with me, or if my self-confidence is just shot from believing there is.

I've done some interesting things - I was in the Peace Corps and I worked with the UN a little, but I can tell when I bring it up I just sound insecure.

First semester I got invited to do things, but I always felt so anxious that I just stayed home most of the time. I don't think I'm disliked, but I do sense that I come off weird sometimes.

While I was in the Peace Corps I read a stupid number of self-help and dating advice books, so I'm embarrassingly well-versed in the theory behind all of it. But I can't really bring myself to be flirty.

There is a pretty Indian-American girl I have a thing for, but I don't know what to do.

I'm working on getting fit, but right now I guess I'm just "skinny-fat". I think I probably look kinda geeky. My hairline's receding, but I have the right haircut (the "Jude Law"). I can talk a lot about the arts, but I've spent my youth exploring such fringe things that it's hard to relate to girls with them (music like hardcore punk and bebop, depressing indie drama movies) - it's like even knowing about that stuff makes me weird or immature, so I tend to keep quiet about it.

What do?