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A first date can be pressure filled. Simple, non-threatening topics are a good way to warm up. You can ease into more serious topics. I love the weather. It might not be the best conversation for a first date, but doesn't it help on those awkward long elevator rides? Or if you happen to smile at someone on the subway? Everyone can talk about the weather. Just don't complain about it; that's boring. After the weather, I adore baseball. I suppose any sport will do, but baseball is my favorite. Any man who watches sports at all will have something to say about one of the following: 1) the team in your town, 2) the team in his old town, 3) the team he loved as a child, 4) the team his mom or dad loved as a child, 5) the Yankees or 6) the Red Sox. Read the sports page the day before the date and you'll be all set.
Conversing in the Zen manner is in direct conflict with my advice to find out critical pieces of information. But it's not! Don't introduce your critical topics but if the conversation starts heading that way, follow it up. For example, if he says, "My parents took us to church all the time when I was a kid." You might say, "Do you still go to church or did they drive you to atheism?"
Try not to dominate the conversation. When I'm nervous, I talk even more than usual (that's a lot) and I have to remind myself to listen to the other person. He has something to say, so give him a chance.
