Small Talk Is Not Small: Questions That Open People Up

Everyone dreads the first-date interview: where do you work, where did you grow up, what do you do for fun, what are you looking for. Both people know the script, both people recite it, and both people leave knowing nothing they could not have read on the profile.

The way out is not to be more interesting. It is to be more curious, and to ask questions that have answers the other person has to think about.

A few that reliably work.

"What is something you were sure about at twenty-five that you have changed your mind on?" This one asks for a small story and a little humility. Almost everyone has an answer, and the answer tells you how they think.

"Who in your family are you most like?" It is warmer than "tell me about your family," and it usually opens onto a mother, a grandfather, a difficult aunt, and a lot of affection.

"What is a small thing that makes a day good for you?" You will learn about morning routines, coffee, music, prayer, gardens, dogs. You will also learn whether the person notices small things, which matters more than it sounds.

"What are you looking forward to this month?" Forward-looking questions tell you whether someone's life has things in it. A person with nothing to look forward to is often a person who is hoping you will be the thing, and that is a heavy job.

"Is there something people get wrong about you at first?" A gentle way to let someone correct an impression. The answers are often the most honest thing said all evening.

Then, and this is the part people skip, listen to the answer and ask the next question about that. If they say they are most like their grandfather, ask what he was like. If they say a good day starts with a walk, ask where. Following the thread is what makes a conversation feel like a conversation and not a form.

Offer answers of your own, briefly, without waiting to be asked. And when you leave, you will know whether you want to see them again, which is the only thing a first date needs to establish.