I live in a pretty sizeable college town (Lexington, Kentucky, with 30,000+ students attending the University of KY alone), but I'm very shy and very bad at approaching people. I asked a girl out in highschool, but we were already friendly and things didn't really work out.
Online dating is a really good means for you to meet someone else. one good free site i can recommend is okcupid.com. Also, gk2gk.com is good too!
I joined okcupid yesterday. Today I messaged someone I thought sounded cool and a different girl who I'd also browsed messaged me, unprompted. I'd browsed her profile before and been intimidated by her looks. We ended up having a pretty decent conversation by IM.