Try asking a few offbeat questions
I've commented that I love it when a new prospect comes up with some creative questions for me, beyond the standard, "How old are you?" and "So what do you do for work?" And, naturally, some of you wrote me to ask for suggestions on these. Now, I'm going to give you a few, some of which people have used on me, and some of which I'm just making up myself right now. I'm not sharing these so you can turn them into stale, overused questions, but to spark your creative thinking.
What's your favorite candy?
When you were a kid, what did you want to be when you grew up?
Is there any popular gift item that someone should never buy for you?
Have you ever broken a bone? Is it a good story? (If it's not, you could try making one up for her.)
Tell me something that you'd share with a stranger but not with your parents.
What's the worst pickup line you've ever gotten? Best?
Where's the strangest place someone's ever tried to pick you up?
(In general, I love questions that show that he's not intimidated or freaked out by the idea that I've flirted with/dated/fucked other guys. On the other hand, these questions can backfire if she's never been at the receiving end of any pickup attempts.)

Comments
My favorite offbeat question (that I use, not that I've gotten) is: "Steak or sushi?" I think you can tell a lot about someone by what they eat. :-)
Posted by: sapiophile | February 5, 2006 8:40 AM