Last night, over a glass of Pinot, I was catching up with a friend who couldn’t believe the questions that she was asked on her latest date. Hint guys: How old are you? What are you measurements? Why are you not married? If you didn’t know, these are inappropriate questions.

If information is what you are seeking (which is completely understandable), there is a smooth creative way to get all the information you could possibly ever want. Instead of asking her age, you can easily ask whether your date knows your friend from their college and determine the class year and do the math in your head.

As for weight and measurements, I’m not sure why that is important, there is either an attraction or there is not. If being a size two is a mandatory requirement, I would revisit your non-negotiables list.
And finally, my favorite, “Why are you not married?” First off, people who live in glass houses should not throw stones. The same question taunts any singleton. And really, isn’t the answer obvious? The person wasn’t ready or just hasn’t met “The One.” I told my friend that I was positive this was meant as a compliment, but nonetheless the question is nonsensical to most women.

Making conversation in the beginning of a date can be tough. Sometimes nervousness brings out statements or questions you wish you’d never said or asked, and in a Seinfeldesque manner, you chase to get them back. (That is why I always advise to go on a second date.) Try to pry the answers you’re looking for out via dialogue instead of pointed questions; you’ll get the same information and avoid walking the tight rope of, “to ask or not to ask?”