TheImage, I hope my advise doesn't sound lame or preachy, but I was in your situation until recently. I was really bummed that everyone around me seemed to have someone. And then I started to change my perspective and my love life really did change. First off, I had to become comfortable with myself. Sure, on paper I had some great qualities, but I really made myself believe it, not just say it. And being happy with myself made me happy to be alone, in a strange way, because if no one was attracted to me, well, why would I want them anyway? My increased confidence finally allowed me to put myself out there and take action. I started talking to people. I gave out my number. I took chances. I'd always been the person who thought what if; I finally decided it was better to have an answer, even an unpleasant one, than a constant state of inaction.
I second the MeetUp approach. Enjoying activities and being social should really help your confidence. And if dating in general weirds you out, don't do it, not in the traditional sense. Instead of going to dinner or coffee with someone, go on a hike or bikeride. Pick something you know you like, someplace you feel comfortable and you. I don't like typical dating stuff, and I always feel uncomfortable. When my boyfriend and I started going out we just decided to be the nerds we were and stay at home and watch tv shows together. And it was perfect because there was no pretense; we were ourselves.
Good luck. I know how hard it can be. Again, I know it sounds SO cheesy but I found that as soon as I just decided fuck it, I like myself and if this works, great, if not, oh well, well, things just came much easier for me.