Find a fellow nerd and go to events together. Make it a project to encourage each other; that is, if I don't muster up the courage to meet someone and start a conversation, then you get a demerit. It's almost uncanny how we will find a way to succeed given a limited scope, easily defined problem.
Once you get into the swing of things, instinct takes over and you'll be fine. You probably have something interesting to discuss with almost everyone else out there. The trick is finding it.
I don't buy into the philosphy of learning about popular culture, sports, or current events just to have something to talk about. Stick with what turns you on; you can be yourself (who else would you be?), and the same thing probably turns someone else on, too.
(Aside: A drink or two couldn't hurt. That's what it's there for.)
I'm with you on taking a buddy - nothing like the spirit of competition to get you over the line.
Tech events are great too - barcamps, meetups etc. You'd be surprised at exactly how many hackers don't just defy the monosyllabic geek stereotype, but smash it out of the park.
We used to play a game in bars and other places, one friend picks a random person and you need to hold that persons attention for X minutes of conversation. Fail to do it and the next round is on you.
Iterate until you are comfortable with it, and can leave your wallet at home.
Once you get into the swing of things, instinct takes over and you'll be fine. You probably have something interesting to discuss with almost everyone else out there. The trick is finding it.
I don't buy into the philosphy of learning about popular culture, sports, or current events just to have something to talk about. Stick with what turns you on; you can be yourself (who else would you be?), and the same thing probably turns someone else on, too.
(Aside: A drink or two couldn't hurt. That's what it's there for.)