21 questions game: how to play, plus 110 questions to ask

“21 questions” means two different games. In the first, one person asks another up to 21 questions to get to know them. In the second, it is a guessing game: one person thinks of something and the other has 21 yes-or-no questions to guess it. Both are easy to play by text or on a video call.

How to play the getting-to-know-you version

1. Decide who asks first.
2. The asker has 21 questions. The other person answers honestly or passes (limit passes to three, so it stays fun).
3. Then swap roles.
4. For a shorter game, each person asks one question at a time, back and forth, until you reach 21 between you.

How to play the guessing version

1. One player thinks of a person, animal, place or object. Say which category it is.
2. The other player asks yes-or-no questions, up to 21.
3. If they guess correctly, they win the round and choose next. If not, reveal the answer and swap.

Good opening questions for the guessing game narrow things down fast: “Is it alive?”, “Is it bigger than a bread box?”, “Could I find it in a kitchen?”, “Is this person real?”

Fun questions

1. What is your go-to snack?
2. What is the best film you have seen this year?
3. If you could have any animal as a pet, what would it be?
4. What is your favourite way to waste time?
5. What is the most random thing in your bag right now?
6. What song do you play when you need energy?
7. Pizza topping you will always defend?
8. What is your most-used emoji?
9. What superpower would you choose, and what is the catch?
10. What is the best meal you have ever had?
11. Morning person or night owl?
12. What show could you rewatch forever?
13. What is the strangest talent you have?
14. If your life had a theme song, what would it be?
15. What is your favourite season, and why?
16. Sweet or savoury breakfast?
17. What is your favourite word?
18. What app do you open first in the morning?
19. What is a trend you never understood?
20. What cartoon character are you most like?
21. What is the best smell in the world?
22. What would you name a boat?
23. Beach holiday or city break?
24. What is your comfort food?
25. What is one thing you would never eat again?
26. If you could be famous for one thing, what would it be?
27. What is the funniest thing that happened to you this month?
28. What game did you love as a kid?
29. What is the best thing you have bought for under ten dollars?
30. Which fictional world would you move to?

Getting to know you questions

1. What do you do for fun on weekends?
2. What is something you are learning at the moment?
3. What is your favourite place you have ever visited?
4. What is a hobby you would like to start?
5. What kind of music do you listen to most?
6. What is the best advice you have been given?
7. What is one thing that always makes you smile?
8. Who do you look up to?
9. What is your idea of a perfect day?
10. Are you more of an introvert or an extrovert?
11. What is something you are really good at?
12. What are you looking forward to this year?
13. Where would you love to travel next?
14. What is your favourite book or the last one you enjoyed?
15. What languages do you speak, or want to?
16. What is a small goal you have right now?
17. What was your favourite subject at school?
18. What would your friends say you are known for?
19. What is your favourite holiday or celebration?
20. Dogs, cats, both or neither?
21. What is a cause you care about?
22. What is a food from your culture everyone should try?
23. What is the best concert or event you have been to?
24. What is your dream job?
25. How do you like to relax after a long day?
26. What is the most interesting thing you have learned recently?
27. What is a movie you think is underrated?
28. Do you prefer calls, texts or voice notes?
29. What is one thing you cannot live without?
30. What was the highlight of your week?

Random and weird questions

1. Is cereal a soup?
2. If animals could talk, which would be the rudest?
3. What would you do if you woke up invisible for a day?
4. Which household object would be the scariest if it were giant?
5. Would you eat a bug for a thousand dollars?
6. What is the best invention nobody talks about?
7. If you had to delete one letter from the alphabet, which one?
8. Which fruit has the best personality?
9. What would your autobiography be called?
10. Would you rather have a rewind button or a pause button for your life?
11. If you were a ghost, who would you haunt, and how?
12. What is the most useless superpower you can think of?
13. Which celebrity would you want as a neighbour?
14. What is the weirdest thing you believed as a child?
15. If you could only speak in one film’s quotes, which film?
16. What colour is Wednesday?
17. Would you go to space if you could come back safely?
18. Which historical figure would be the worst at a party?
19. What is a sound you cannot stand?
20. What food would you be, and why?
21. If you could rename the planet, what would you call it?
22. What would you do with a pet dinosaur?
23. Which chore would you pay anything never to do again?
24. What is the worst name for a restaurant you can think of?
25. If your pet could text you, what would they say?
26. Would you rather fight one horse-sized duck or ten duck-sized horses?
27. What is the most overrated food?
28. Where would you hide during a zombie outbreak?
29. If you were a flavour of crisps, what would you be?
30. What would be the worst thing to hear from a pilot mid-flight?

Deep questions

1. What is something you believed five years ago that you do not believe now?
2. What does a good life look like to you?
3. What is your biggest fear, really?
4. When did you last feel truly proud of yourself?
5. What is a mistake that taught you something important?
6. What would you do if you knew you could not fail?
7. What do you value most in a friendship?
8. What is something you are still figuring out?
9. What moment would you relive if you could?
10. What makes you feel at peace?
11. What is a part of your personality you have grown into?
12. Who has had the biggest influence on you?
13. What is something that always gives you hope?
14. If you could ask your future self one question, what would it be?
15. What is something small that means a lot to you?
16. What do you wish more people understood?
17. What would you change if you could restart the last year?
18. What makes a conversation feel meaningful to you?
19. What is your definition of happiness?
20. What is a belief you hold that most people might disagree with?

Guessing game ideas

For the guessing version, pick things most people know. Some starters: a giraffe, a toothbrush, the Eiffel Tower, a rainbow, a penguin, a pizza, the Moon, a violin, a lighthouse, a cactus, a rollercoaster, a snowman, a library, a volcano, a paper clip, a football, a hot air balloon, a honeybee, an umbrella and a chess board. Guessing a famous person is fun too, as long as both of you know them.

Tips for playing with someone new

• Start with light questions and save deep ones until you are both enjoying it.
• Answer your own questions too. It makes the game feel like a conversation, not an interview.
• Keep personal details private. Talk about your interests and opinions, not your name, school, workplace or where you live.
• Follow up. If an answer is interesting, ask “why?” before moving on. It does not have to count as a question.

You can try it in a random text chat or on video: suggest “want to play 21 questions?” and let the other person ask first. For more ideas, see get to know you questions and random questions to ask.