I agree with the most recent poster. Just ask questions! It's the easiest way to get them talking and see whether they bring something up that you can latch on to. Even a vague "why don't you tell me a bit about yourself?" Will get a person talking. I did the online dating thing, and honestly, the people who were really suave creeped me out. It was the ones who were kind of awkward and a little bumbling and didn't know quite what to say that I wanted to meet and really liked. It showed me that they were real people who actually wanted to meet someone and were interested in more than a hook-up. Just stick to questions if you're not sure what to say, then offer a genuine comment to their answers. Something simple like, "Oh, you like soccer? There are some great parks near here." or whatever. Good luck! Also, if it would help, feel free to send me a message on here if you want to practice conversationaling! (Is that even a word?) Then you can get some practice in, ease your nerves, and there's no pressure because it's not someone you're looking at as a prospective date.