> This is compounded with the fact that like a lot of other techy people I was awkward with the opposite sex in high school.
Same here.
> I have interesting hobbies, go out every now and then (mostly to concerts), I'm trying to dress better, and I work out a few times a week (which has done wonders for my self confidence).
Bingo. You need to be in a place where you are satisfied. Not happy. Nobody can be happy alone. But satisfied that you are leading the life that you want.
Very few people get that chance in life. To truly lead the life they want and desire for themselves.
> But hey, if you've got any dating advice I'm definitely willing to listen.
Get into a habit of doing one new thing a day. Even things you're uncomfortable with. Just by virtue of doing that, you'll end up meeting new people and will begin to see things in a new light. It'll also make your life more interesting and fun.
Dating advice? Keep it simple. Figure out what you want. Go after it. Don't give up, keep pushing forward.
If you really want a girl your age, go after that. I know you convinced yourself they're all in college. They're not. There are plenty of women who didn't go to college and went into a profession directly, just like you. Models come to mind. Want to date a model?
Think about this again and again, until you realize you are not at a disadvantage, but are actually so far ahead of the pack, you can't even see the losers behind you. Seriously.