Man: What do you like to do?
Woman: I like reading. What about you?
Man: What do you like eating?
Woman: What about you?
How can a guy who isn't exactly the best conversationalist at first get his date to open up and talk about herself? Any ideas ladies?
If you can, bounce a follow-up question or two. If she likes to read, you can ask her what she likes to read -- favorite authors, types of books or publications, and so on. If you can avoid "Yes" or "No" questions, so much the better. Open-end questions tend to lead to conversations, not just quickie one-word responses.
Assuming this date would be with a CM lady, review her profile. It should give you some clues about where to start a conversation. It's helpeul if there are some mutual interests about which both of you are enthusiastic. Also, if you met online, the topic of online dating is good for starters. Perhaps both of you have reservations about it because it's the first time you've tried it. What are her feelings about it?
Try to sound interested in really knowing the answers to what you're asking. Just blandly rattling off a bunch of questions isn't going to spark a lively conversation. If it sounds like an interrogation, your date will most likely feel uncomfortable.
There was something that interested you in the first place. You might be able to capitalize on that. What brought you together in the first place? Something grabbed your attention. Let her know what it was.
Easy to say: try to relax and be yourself. It's easier than putting on an act. Above all, do your best to put your date at ease. If she's not comfortable with her surroundings or your intensity of questioning, she might not hope for a second date.