21 questions

Pick who's playing and how bold to go, and we'll deal 21 questions for one person to answer.

Who are you with?
What mood?

  1. Pick who answers first.
  2. The others take turns asking until all 21 are done.
  3. Answer honestly and skip one at most. Then swap.

All 74 questions for the game

Light

  1. What was your first job?
  2. Can you quote a whole movie almost word for word? Which one?
  3. Who was your celebrity crush growing up?
  4. Which fictional world would you move to tomorrow?
  5. Did you have a nickname growing up? Where did it come from?
  6. Which pet peeve drives you up the wall?
  7. What's the last photo you took that you'd happily show everyone?
  8. Has anyone ever told you that you look like someone famous?
  9. Which three things would you take to a desert island?
  10. What's your go-to karaoke song?
  11. Would you ever go on a trip with a group of strangers?
  12. If you could be 20 in any decade, which would you pick?
  13. Who did you see at your first concert?
  14. Name the weirdest thing in your fridge right now.
  15. If you could swap jobs with anyone for a day, who would it be?
  16. How embarrassing was your first email address?
  17. What do you always carry in your bag?
  18. Which TV family is most like yours?
  19. If you were an animal, which one would you be?
  20. As a kid, what did you believe that turned out to be completely wrong?
  21. Would you ever dye your hair bright blue?
  22. Which everyday thing are you surprisingly bad at?
  23. Where did you go on your first trip without your parents?
  24. Is there a chore you secretly enjoy?
  25. What's the most impulsive thing you've ever bought?
  26. Which word from your hometown does nobody else seem to get?
  27. What was the first thing you ever cooked on your own?
  28. Have you ever read the last page of a book first?
  29. Describe the weirdest dream you can still remember.
  30. Who's the most famous person you've ever met?
  31. Which emoji do you overuse?
  32. What's the longest phone call you've ever had, and who was it with?
  33. What would people be surprised to hear you've never done?
  34. How bad was your worst haircut?
  35. Would you ever drop everything to open a tiny shop? What would it sell?
  36. When you get home, what's the first thing you do?
  37. If you got a superpower that only worked on Tuesdays, which would you pick?
  38. Who's the funniest person you know?

Deep

  1. Who knows you better than anyone?
  2. What makes you lose track of time?
  3. Which piece of advice do you give people most often?
  4. Which book changed your mind about something?
  5. What are you most curious about right now?
  6. How long have you known your oldest friend?
  7. What do you find beautiful that other people walk right past?
  8. When do you feel most confident?
  9. Who's someone you've never properly thanked?
  10. Which lesson took you way too long to learn?
  11. Which skill did you teach yourself that you're proud of?
  12. Which compliment would you love to hear more often?
  13. What's your favorite memory of us?
  14. What do you hope never changes between us?
  15. Name one thing you'd love us to do together this year.
  16. What are you grateful for today?
  17. If every day had one extra hour, how would you use it?

Bold

A little daring, never explicit

  1. When did you last get butterflies over someone?
  2. When did you last tell a white lie, and what was it?
  3. Have you ever made the first move? How did it go?
  4. What's the most cringey thing you did as a teenager to look cool?
  5. What's a rumor about you that turned out to be true?
  6. What makes you blush?
  7. Out of 10, how good is your flirting?
  8. Where did your first kiss happen?
  9. Which song would you dedicate to your crush right now?
  10. What's a tiny thing that's an instant dealbreaker for you?
  11. What's the cheesiest thing you've ever done for someone you liked?
  12. What's a dare you'd say yes to right now?
  13. Have you ever written a love letter, or gotten one?
  14. What's something you find attractive that most people don't?
  15. What's your most controversial food opinion?
  16. Have you ever been asked out by a total stranger?
  17. What's the most embarrassing thing you've done in front of a crush?
  18. Have you ever had a crush on one of your friends?
  19. What's the boldest thing you've ever worn in public?

Questions about the questions

How do you play 21 questions?

One person answers 21 questions in a row while the others take turns asking. Answer honestly, skip one at most, then swap. With two people, like on a date, you can take turns question by question instead.

Can you play 21 questions on a date?

Yes. Tell the generator you're with a date, and the questions stay a little flirty at most, never explicit.

Try them on new people

Every week Timeleft seats small groups of strangers for dinner, coffee or a walk, with conversation prompts built in.