You're at a cozy coffee shop, eating a lovely dinner or taking a pleasant walk. What do you talk about? The worst thing to talk about is your romantic past. Ideally you should avoid certain topics (exes, sexual exploits, neuroses, problems with your parents).
But if it's me, I'm talking about old boyfriends. The harder I try to avoid the topic, the worse it is. I like to tell stories and my best stories are about old boyfriends or bad dates. I don't only have old boyfriend stories. I have great stories about my early childhood. I can talk for a long time about the politics of graduate school and my teaching experiences. I can explain, in detail, how the federal bureaucracy works. I have a lot to say about SAS programming. Thus, I feature the old boyfriend stories.
A forced conversation is much worse than talking about old boyfriends. The best approach is "Zen." Make your mind a blank and see what happens. (Is that Zen? Whatever.) If you are nervous and shy, you might think of one or two questions to ask ahead of time, but please don't make a list. If you do make a list, memorize it and don't carry it with you. My favorite topics include, "Where are you from?" "What kind of work do you do?" "What was the last good movie you saw?" I'm not too fond of "What are you looking for in a relationship?" "What's your favorite movie/book/band?" (Too much pressure. I have answers, but I hate to answer.) "What do you do for fun?" Boring!
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.
Here are some conversational blunders from past dates:
- He said, "I've been talking a lot--now it's your turn!"
My reaction: If you want to draw me out, ask questions.
What I said, "It doesn't work that way. I'll talk when I have something to say. I'm happy listening for now."
- He said, "You don't seem very interested in me. Do you want to ask me any questions?"
My reaction: No. If I'm talking a lot I'm nervous. It's a first date, so cut me some slack!
What I said, "I'm sorry, I thought we were just having a regular back and forth. Weren't you talking too? I didn't mean to talk so much. It doesn't mean I don't like you." (Irony, sometimes all that talking does mean I don't like you! Sometimes it means I do like you! Good luck untying that knot.)
- He said, "I'll tell you anything you want to know, just ask."
My reaction: If you want to tell me something, tell me. Jump in, the water's fine.
What I said, "Uh, um, uh. I dunno."