Questions to ask your friends

If you had to introduce me to a stranger using only my three worst habits, which would you pick?

Limiting it to three forces a ranking, and the ranking is the joke. Ask only if you can hear 'always late' without launching a defense.

From: Questions to Ask Your Best Friend

Which place from your past no longer exists the way you remember it?

A demolished school, a sold house, a field that became a parking lot. It carries some weight, so ask it when the mood has already slowed down.

From: Questions to Ask Your Friends

If you could have a superpower that only worked while you were embarrassed, what would you want?

The constraint forces people to describe a recent embarrassing moment to justify their choice, which is the real payoff of the question.

From: Dumb Questions to Ask Friends

If you could only eat one food for the rest of your life, what would it be?

Everyone picks something they love and then talks themselves out of it once they imagine day forty. The fun is watching a person negotiate with their own answer in real time.

From: Dumb Questions to Ask Friends

What could you talk about for an hour without getting bored?

Better than asking about hobbies because it licenses enthusiasm. People are noticeably more themselves while answering it.

From: Questions to Ask Your New Friends

What are you working on at the moment, in or out of work?

Present tense, so you have something specific to raise next time you see them. The in-or-out-of-work part also catches people whose real life is a side project rather than their job.

From: Questions to Ask Your New Friends