What to ask on a first date

The commonest first date failure is two people taking turns to interview each other. Job, kids, where you live, what you do at weekends — all answered, nothing learned, both bored.

What makes a question good

It cannot be answered in three words, it is not about credentials, and answering it tells you something about how the person thinks rather than what they have done.

Questions that work

• What are you looking forward to at the moment?
• What is something you have changed your mind about?
• What did you want to be when you were twelve?
• What is the best thing you have watched or read lately, and why that one?
• What is something you are unreasonably good at?
• What would you do with a free Saturday and nobody to answer to?
• What is the last thing that genuinely surprised you?

None of these is clever. They are just open, and open is the whole trick.

Questions to leave

• Anything about their divorce or bereavement. If they raise it, listen. Do not ask.
• Money, in any form. Including what they do, if it is really about earnings.
• Their last relationship and why it ended.
• What they are looking for, asked as a test rather than out of interest.
• Anything about their children beyond the basics, on a first meeting.

The thing that matters more than questions

Following up. “Why that one?” and “What was that like?” do more work than any question on any list, because they signal that you were listening rather than waiting for your turn.

People consistently describe the best first dates as ones where they felt heard. Almost nobody describes them as ones where the other person asked good questions.