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21 Questions

Pick a player, then ask them twenty-one questions in a row. By the end, the group knows them better than they expected.

2+ players 15-45 minutes108 prompts No sign-up
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21 Questions puts one person in the spotlight and asks the rest of the group to be curious about them for a few minutes. The format is fixed: choose a player, then ask them exactly twenty-one questions, one after another, with short honest answers and no long detours. When the count reaches twenty-one, the spotlight passes to someone else, and the previous player gets to ask the first question of the next round. Twenty-one is a deliberately awkward number. It is long enough that the easy questions run out and the group has to think, and short enough that nobody gets tired of being the subject. Every player is allowed to pass on three questions.

All 108 21 questions game

Funny (27)

  1. What is the most ridiculous thing you own?
  2. What would you do first if you woke up ten feet tall?
  3. Which chore do you do badly on purpose?
  4. What is your least convincing lie?
  5. If you had to wear one outfit for a year, what is it?
  6. What food would you refuse even for a prize?
  7. Which emoji describes your last week?
  8. What is the worst advice you have ever given?
  9. Which everyday task takes you far too long?
  10. What is the strangest compliment you have received?
  11. If your pet could speak, what would it complain about?
  12. What is your most useless collection?
  13. Which app do you delete and reinstall constantly?
  14. What would be on the menu at a restaurant you designed?
  15. Which sound do you make when you are concentrating?
  16. What is the most embarrassing song you know every word to?
  17. If you had a warning label, what would it say?
  18. What is the last thing you broke by accident?
  19. Which fictional job would you be terrible at?
  20. What is your signature dance move?
  21. Which board game brings out your worst side?
  22. What would you do with a hundred balloons?
  23. Which nickname have you never escaped?
  24. What is the weirdest thing in your kitchen right now?
  25. If you had to give a speech with no notice, what topic would you pick?
  26. What is the smallest thing that has ever annoyed you enormously?
  27. Which household item do you always lose?

Deep (27)

  1. What are you most curious about right now?
  2. Which failure taught you the most?
  3. What do you want people to say about you in ten years?
  4. How do you decide what to say yes to?
  5. What is a value you hold that costs you something?
  6. When do you feel most confident?
  7. What is a fear you have mostly outgrown?
  8. Which advice do you give often but follow rarely?
  9. How do you know when something is finished?
  10. What would you do differently if nobody was watching?
  11. What has been the hardest thing to be patient about?
  12. Which of your strengths came from a difficulty?
  13. What do you find beautiful that others overlook?
  14. How do you want to spend your time in five years?
  15. What is something you have changed your mind about completely?
  16. Which relationship in your life do you want to invest more in?
  17. What do you do when you feel stuck?
  18. Which part of your life feels most yours?
  19. What is the most generous thing anyone has done for you?
  20. How do you define a good day?
  21. What are you avoiding learning?
  22. Which mistake do you keep repeating?
  23. What kind of pressure brings out your best work?
  24. When did you last feel completely absorbed in something?
  25. What do you think you will care about at seventy?
  26. Which of your opinions is hardest to explain to others?
  27. What is worth doing badly?

Favorites (27)

  1. Favorite meal you can cook from memory?
  2. Favorite place you have ever slept?
  3. Favorite month of the year, and why?
  4. Favorite film you would rewatch tonight?
  5. Favorite way to spend an hour alone?
  6. Favorite thing you own that cost almost nothing?
  7. Favorite smell?
  8. Favorite thing about where you live?
  9. Favorite book you have finished more than once?
  10. Favorite time of day?
  11. Favorite piece of clothing in your wardrobe?
  12. Favorite sound in an ordinary day?
  13. Favorite drink, hot or cold?
  14. Favorite thing to do with a free weekend?
  15. Favorite way to travel a long distance?
  16. Favorite game, of any kind?
  17. Favorite person to get advice from?
  18. Favorite holiday you have taken?
  19. Favorite thing you learned this year?
  20. Favorite word in any language?
  21. Favorite kind of weather to walk in?
  22. Favorite dessert, no hesitating?
  23. Favorite room in any building you have been in?
  24. Favorite thing about your closest friend?
  25. Favorite album to play start to finish?
  26. Favorite subject you never studied formally?
  27. Favorite thing you have made with your hands?

Hypothetical (27)

  1. If you could restart one year of your life, which?
  2. If you had to run a museum, what would it display?
  3. If you could only travel by train forever, where would you go first?
  4. If you had to choose a completely new name, what would it be?
  5. If you could invite three people to dinner, who is at the table?
  6. If you had unlimited time but not money, what changes?
  7. If you could remove one invention from history, which?
  8. If you had to live in one building for a decade, what building?
  9. If everyone had to learn a craft, which should it be?
  10. If you could be excellent at one sport, which?
  11. If you had a week with no obligations, describe the first day.
  12. If you had to choose the soundtrack for your city, what plays?
  13. If you could keep one season all year, which?
  14. If you were made mayor tomorrow, what is your first decision?
  15. If you had to give away everything but one room's worth of things, what stays?
  16. If you could read every book on one subject, what subject?
  17. If you had to work outdoors permanently, what job would you take?
  18. If you could speak with an ancestor for an hour, what would you ask?
  19. If you could make one law that everyone accepted, what is it?
  20. If you had to spend a year on a small boat, who is with you?
  21. If your name became a verb, what would it mean?
  22. If you could design a public holiday, what does it celebrate?
  23. If you had to teach one class every week, what subject?
  24. If you could see one statistic about your own life, which?
  25. If you had to pick a completely different hometown, where?
  26. If you could solve one problem in your field, which one?
  27. If you had to give a stranger one useful item, what would it be?

How to play

  1. Choose one player to be the subject of the round.
  2. The rest of the group takes turns asking questions from any category, counting them aloud.
  3. The subject answers in a sentence or two and may pass on up to three questions.
  4. At twenty-one, pick a new subject and start the count again.

Frequently asked questions

Why twenty-one questions?

It is long enough to get past the obvious questions and short enough to keep every player's turn under ten minutes.

Can the subject refuse to answer?

Yes, three passes per round. A passed question does not count toward the twenty-one.

Does it work with only two people?

It works well. Take alternating rounds so each person gets a full twenty-one as the subject.

Want questions with right answers?

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