Interesting Questions
For people who would rather skip “so what do you do?” These reward curiosity and strong opinions, perfect for dinner parties, long drives, and second dates.
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What’s something small that always makes your day better?
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Curiosity and ideas
Opinions, knowledge, rabbit holes.
- 01What's something you know a surprising amount about?
- 02What's the most interesting place you've ever worked or studied?
- 03If you could master any subject overnight, what would it be? Try asking: What would you do with that skill first?
- 04What's a rabbit hole you recently fell into online?
- 05What's something the world would be better off without?
- 06What's the coolest thing you've made or built?
- 07What historical period would you want to visit for a week?
- 08What's a documentary everyone should watch?
- 09What's an opinion you held strongly and then completely flipped on?
- 10What's the best museum you've ever visited?
- 11What invention do you think changed everyday life the most?
- 12What's a language you'd love to speak fluently?
- 13What's something you believed as a kid that turned out to be wrong?
- 14What's the most beautiful place you've seen in person?
- 15What question do you love being asked?
- 16What's a tradition from another culture you admire?
- 17What's the best piece of trivia you know?
- 18If you could interview anyone alive, who would it be?
- 19What's a city you could explore for weeks without getting bored?
- 20What unsolved mystery fascinates you the most?
- 21Are you more competitive or cooperative?
- 22What food reminds you of home?
- 23An artist you love that nobody else seems to know?
- 24What movie ending would you rewrite?
- 25What hobby do you think everyone should try once?
- 26What small thing do most people underestimate?
- 27What norm from ten years ago already feels ancient?
Stories and experience
Travel, taste, things made.
- 01What's been on your mind a lot lately?
- 02What's something exciting happening in your life? Try asking: What is the best thing that could happen there?
- 03What's a story your friends always ask you to retell?
- 04What are you reading, watching, or listening to right now?
- 05What's something you're hoping the next few months bring?
- 06What's the best thing that happened to you this month?
- 07What's a question you wish strangers asked instead of small talk?
- 08What's a place that feels like home to you?
- 09What's something you could give a short speech about with no prep?
- 10What's your favorite thing to do when you have zero plans?
- 11What's a belief you picked up from your family?
- 12What's the story behind where you live now?
- 13What's a challenge that taught you something important?
- 14What's your favorite holiday and how do you spend it?
- 15What's something you're looking forward to learning?
- 16What is the best dinner conversation you have ever had?
- 17Where would you move tomorrow if work allowed it?
- 18What is the highlight of a normal Tuesday for you?
- 19What is your favorite thing to do after midnight?
- 20Who has believed in you when you did not?
- 21If you had to teach a class tomorrow, what would it be?
Good to know
Getting more out of these questions
- Start light and get more personal as the conversation warms up.
- Follow the interesting answer, not your list. One good follow-up beats three new questions.
- Share your own answer too, conversation is a trade, not an interview.
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Frequently asked questions
What is the difference between deep and interesting questions?
Interesting questions explore ideas and experiences; deep ones explore feelings and values. Interesting is safer with new people.
How do I handle strong opinions?
Get curious before disagreeing: “What changed your mind on that?” keeps it a conversation, not a debate.