I have been on one date in my entire life, and I would not count it as being anything remotely resembling successful.
I was thinking over it, and I realised why I have so much trouble talking to people I don't know. I don't have anything to talk about. While as a geek I tend to know a bit of everything, the only things I can really talk about in any form of depth is work and roleplaying. They are really the only things I have any real familiarity with.
I don't follow any sports, I don't care about celebrities, I read the news but don't look at it in much depth, I don't watch TV or movies, and most of my music is stuff that I've liked for a while, so I have no idea of much of the newer stuff. So, my choices are talk about work (which would make me look like a work-a-holic, and is probably as boring a bat-shit) or roleplaying, and that ain't going to work unless I happen to be talking to another roleplayer (and to be honest, I really don't think I want to have most of the discussion talking about "my character").
I really need to get involved in a socially acceptable hobby that can be used as a topic of conversation. As I get to know someone, I'm better at talking with them, but even so, most of my conversations are limited to work, roleplaying, or other mutual friends. What else can I talk about?
So, does anyone have any suggestions on how to feel comfortable talking to strangers, especially with my limited knowledge base?