21 Questions Game: Rules and 84 Questions to Ask

How to play 21 questions

1. Decide who asks first.
2. Ask one question. The other person answers honestly.
3. Swap: they ask you a question.
4. Keep going until 21 questions have been asked (or 21 each, if you want a longer game).

Common house rules: each player gets one skip, you can’t ask a question that was already asked, and follow-up questions count toward the 21. It works in person, on a date or over text.

A few popular variations:

• Same question rule. Whoever asks a question has to answer it too. Good for a first date, when both people are a little guarded.
• Lightning round. One-word answers only, no explaining. Great for the first five questions.
• Group version. Sit in a circle and ask the person on your left. Each person answers three questions before passing.

Questions to get to know someone

1. What’s your go-to comfort food?
2. What’s the best trip you’ve ever taken?
3. Are you a morning person or a night owl?
4. What’s a hobby you’d pick up if you had more time?
5. What’s the last show you binge-watched?
6. What did you want to be when you were a kid?
7. What’s your hidden talent?
8. Would you rather spend a weekend in the city or in the mountains?
9. What’s your favorite way to spend a Sunday?
10. Who’s the funniest person you know?
11. What’s a skill you’re weirdly proud of?
12. What’s the best concert you’ve been to?
13. What’s your most controversial food opinion?
14. Do you have any irrational fears?
15. What’s the best compliment you’ve ever received?
16. What’s on your bucket list for this year?
17. What’s the most interesting job you’ve ever had?
18. What’s your favorite smell?

Questions to ask a guy

These work on a date, over text or with a friend you want to know better. Open-ended questions beat yes-or-no ones every time.

1. What’s something you’re really competitive about?
2. What’s the best piece of advice your dad or a mentor gave you?
3. What’s your most embarrassing moment from high school?
4. What’s the most spontaneous thing you’ve ever done?
5. What do you notice first when you meet someone?
6. What’s your idea of a perfect first date?
7. What’s a movie that made you emotional, even if you won’t admit it?
8. What’s something you’ve never told your friends?
9. Do you think you’re a good cook? Prove it with one dish.
10. What’s a goal you’re working on right now?
11. What makes you feel most confident?
12. What’s a small thing that instantly makes your day better?
13. What’s your biggest pet peeve in other people?
14. What’s one thing you’d change about your life right now?
15. What’s a game, sport or team you’ll always defend?

Questions to ask a girl

Same idea: curious, specific and easy to answer with a story rather than a single word.

1. What’s a song you could listen to on repeat forever?
2. What’s your favorite memory from childhood?
3. What’s something that always cheers you up?
4. What’s a place you’ve always wanted to visit?
5. Who do you look up to most?
6. What’s your love language?
7. What’s the most adventurous thing you’ve ever done?
8. What’s a book or movie that changed how you think?
9. What’s your favorite thing about yourself?
10. What’s an unpopular opinion you’ll defend forever?
11. What’s the best thing that happened to you this week?
12. What do you do when you need to recharge?
13. What’s a small gesture that means a lot to you?
14. What’s something you’re looking forward to?
15. What’s a trend you never understood?

21 questions for couples

Already together? These dig into the relationship itself.

1. What was your first impression of me?
2. When did you know this was serious?
3. What’s your favorite thing we do together?
4. What’s one thing I do that makes you feel loved?
5. What’s a tradition you want us to start?
6. What’s your favorite memory of us so far?
7. What’s something you want us to try this year?
8. What’s the best gift I’ve given you?
9. What would your perfect day with me look like?
10. What’s something about me that surprised you?
11. What song reminds you of us?
12. Where would you want to live together if money didn’t matter?
13. What’s one thing you’d like me to understand better about you?
14. What’s our funniest moment as a couple?
15. What’s a small habit of mine you’d miss if it stopped?
16. What’s one thing you’d want us to never stop doing?

Deep questions for 21 questions

Save these for when the conversation is already flowing.

1. What does a happy life look like to you?
2. What’s something you’ve changed your mind about in the past few years?
3. What’s the hardest thing you’ve ever gone through?
4. What do you value most in a friendship?
5. What’s a fear that holds you back?
6. Who has had the biggest influence on who you are?
7. What’s something you wish more people knew about you?
8. What are you most grateful for right now?
9. If you could talk to your younger self, what would you say?
10. What’s a belief you hold that most people around you don’t?
11. When do you feel most like yourself?
12. What’s something you’re still trying to forgive yourself for?
13. What do you think happens after we die?
14. What would you do differently if you could start over?
15. What does love mean to you?
16. What’s one thing you want to be remembered for?
17. What’s a risk you’re glad you took?
18. What’s the most important lesson life has taught you so far?
19. What makes you feel truly understood?
20. What’s a question you wish people asked you more often?

Tips for a better game

1. Start light, go deeper. Open with a few easy questions before the deep ones, or answers stay short.
2. Ask a follow-up. The best moments come from “Wait, why?” Decide up front whether follow-ups count toward 21.
3. Answer your own question too. It keeps things balanced and stops it from feeling like an interview.

Want a game that asks the questions for you?

If you’d rather not come up with questions yourself, Duoo has games that work just as well with two people on one iPhone. Would You Rather sparks quick debates, Never Have I Ever gets the stories out, and Who’s Most Likely To is great for couples. For more ideas, see our lists of truth or dare questions for couples and games for couples to play on your phone.