21 Questions game: Dig deep with these 165 fun, flirty and surprising questions (2024)

Want to get to know someone on a deeper level? Playing a round of the classic 21 Questions game is a great reason to ask all the right questions to get to know someone better, whether that person is your best friend or your crush.

So the next time you’re in need of a fun (and free!) game to play with friends, just pull up this list of 21 Questions game questions. We’ve rounded up the most interesting—and the silliest, and the flirtiest—questions to ask to help you spark great conversations about anything and everything. With fun questions like these at your fingertips, you’ll literally never run out of things to talk about.

Let the games—and the conversation starters—begin!

How to Play the 21 Questions Game

Playing 21 Questions is super simple and straightforward, and you can play it with as many people as are in your group.

If you’re playing with two people, you and the other person can simply take turns answering questions. You can also modify this by having one person answer several questions in a row (or all 21 questions) before reversing roles and having the other person answer questions. That said, if you’re playing 21 Questions during a date, especially an early-on one, it’s probably going to feel better and more natural to take turns answering. You don’t want one person to wind up hogging all the airwaves!

If you’re playing in a group, the first player can choose a question from the following list of 21 questions to ask (and then some). Then, the group can go around one by one and answer that question, with the person who asked the question going last. After everyone answers, the next player chooses a question and everyone answers again, and so on.

You can set rules that allow each player to skip a turn (or multiple turns) if they don’t feel comfortable with the question, or you can play in hard mode and make it mandatory to answer every single question. It’s ultimately up to you, but keep in mind that if anyone appears super hesitant to answer a specific question, it’s not kind to force them. Consider giving that person an out and keeping the game rolling. If a question comes around that you feel embarrassed to answer, you’ll be glad you set the precedent of letting others off the hook.

Now, onto the list of questions. Ahead, you’ll find more than 21 questions to ask (gotta account for those potential skips), including some additional flirty questions that are perfect if you happen to be playing with a crush.

21 Questions List

From deep questions that’ll spark an honest dialogue to unique and random questions we’re pretty sure your game-mates won’t have heard before, choose any 21 (or more) of the following queries for your 21 Questions game.

1. What’s the weirdest dream you’ve ever had?

2. If you could travel to any time period in a time machine, what time period would you choose and why?

3. If you could change one thing about yourself, what would it be?

4. When asked what your most fun memory from childhood is, what’s the very first memory you think of?

5. If you could have any fictional character’s wardrobe, whose would it be?

6. What was the first job you ever wanted to have as a kid?

7. If you could have dinner with a famous person (living or dead), who would you choose?

8. What’s your favourite movie to watch over and over again?

9. You’re the lead character in a video game. What game is it? (You’re allowed to make one up.)

10. What’s your favourite season of the year?

11. If you could create your own holiday, what would it be called and how would it be celebrated?

12. Who is your current celebrity crush?

13. What’s the most random thing you’ve ever bought online?

14. If you could invent any gadget, what would it do?

15. What’s the worst thing you’ve done to get out of trouble?

16. Do you have a favourite museum? Which one?

17. What’s your biggest fear?

18. What’s the most adventurous thing you’ve ever done?

19. What’s the best advice you’ve ever received?

20. You were just handed 1 crore to open your own business. What kind of business is it?

21. What’s a bad habit you had that you’ve been able to overcome?

22. What’s your dream road trip destination?

23. What’s your favourite food of all time?

24. What are three items on your bucket list?

25. What’s your biggest regret?

26. The only way you can communicate is through movie quotes. What movie are you choosing?

27. What’s your favourite urban legend?

28. What’s your favourite thing about yourself?

29. What’s the weirdest thing in your closet?

30. If you had to guess what people appreciate about you the most, what would you say?

31. What’s your dream job?

32. If you could be a part of a family on any TV show, which family would you choose?

33. Of all the personal questions I could ask you, what’s one you wouldn’t want to answer?

34. What’s your biggest pet peeve when it comes to social media?

35. Who’s your favourite character from literature?

36. What’s an activity that you do not find fun at all?

37. What’s the weirdest thing you’ve ever done for a job?

38. What’s the most recent thing in your internet search history?

39. What’s the last thing in your phone that you took a screenshot of?

40. What’s your favourite colour to wear?

41. What’s your favourite type of dessert?

42. What’s the worst lie you ever told as a kid?

43. Who in your family are you closest to?

44. What’s your favourite sport to play and why?

45. If we were in the middle of a zombie apocalypse, who are three people you’d want on your team?

46. If you were an ice cream flavour, what would it be?

47. What’s your favourite song to sing in the shower?

48. What’s one thing your mom or dad doesn’t understand about you?

49. If you had a kid, what would you name it?

50. What’s your moon sign?

51. You’ve just walked into a shopping mall. Where’s the first place you’re going?

52. What’s your favourite way to spend a day off?

53. What’s a skill you’d love to learn?

54. This or that: Living by the sea or living in the mountains?

55. What do you want your funeral to be like?

56. What’s a tattoo you want to get? Name the first one that comes to mind.

57. What app do you spend the most time on?

58. What do you think the No. 1 most important quality in a friend is?

59. What’s an unpopular opinion you have that you actually feel really strongly about?

60. What’s your favourite thing about your hometown?

61. What’s the best compliment you’ve ever received?

62. What’s your favourite way to celebrate your birthday?

63. Do you have any phobias?

64. What was your first-ever concert?

65. Who was your first favourite musical artist?

66. If you could have any job for a day, what would it be?

67. What’s your favourite type of movie snack?

68. What’s your favourite piece of random trivia? You can only choose one.

69. What’s the best decision you’ve ever made?

70. What’s the most important lesson you’ve learned from a mistake?

71. Do you have a favourite podcast?

72. What’s the best vacation you’ve ever been on?

73. What’s your favourite memory from the past year?

74. What’s your favourite thing about your best friend(s)?

75. What’s your favourite way to give back?

76. You’ve just been granted a treat-yourself-day with three wishes. What are they, and how are you spending the day?

77. What’s the last new thing you learned? It can be a skill or a fact.

78. What’s the worst first date you’ve ever been on?

79. What character are you in Mario Kart?

80. What’s the most spontaneous thing you’ve ever done?

81. If you could live in any fictional world, which one would it be?

82. What’s your favourite conspiracy theory?

83. If you could instantly master any instrument, which one would you choose?

84. What’s the most unusual talent you have?

85. What’s the most interesting class you’ve ever taken?

86. What’s the most bizarre coincidence that’s ever happened to you?

87. If you could live in any country for a year, where would you go?

88. If you could be a fly on the wall, where would you land?

89. What’s the best prank you’ve ever played on someone?

90. If you could design a theme park, what would it be like?

91. What’s the most out-of-character thing you’ve ever done?

92. What’s the most unusual tradition in your family?

93. What’s the best gift you’ve ever received?

94. What’s the weirdest superstition you secretly believe in?

95. What movie has made you laugh hardest?

96. What’s the most ridiculous thing you’ve ever bought?

97. If you could instantly be an expert in one subject, what would it be?

98. If you could have any fictional character as a best friend, who would it be?

99. You’re writing your will. What are you bequeathing to whom?

100. If you could relive one day of your life, what day would it be?

101. If you could have any artist, dead or alive, perform at your next birthday, who would it be?

102. What’s the weirdest thing you believed as a child?

103. If you could live in any house from a TV show or movie, which one would you choose?

104. If you could have any one item of immense value in your home, what would it be?

105. If you could swap lives with any historical figure, who would it be?

106. What weird combination of foods do you secretly love?

107. Would you rather personally explore the deep sea or outer space?

108. What’s your favourite fun fact about an animal species?

109. Do you believe in magic?

110. If you could turn any hobby into a profession, what would it be?

111. If you could create your own podcast, what would it be about?

112. You were just handed a free one-way airplane ticket to any destination of your choosing. Where are you going?

113. What’s the best thing you’ve ever found at a flea market, antique store or yard sale?

114. What’s the best ghost story you’ve ever been told?

115. You can take one trait or ability from any animal or insect. What are you choosing?

Bonus: Flirty questions to ask your crush

These intimate 21 Questions game questions work especially well for a love interest, since they’re all romance-related (and some are even a little sexy). If you’re playing with your crush or on a first date, consider these flirty questions your go-to.

1. Do you believe in love at first sight?

2. What was your first kiss like?

3. What was your best kiss like?

4. What was your first impression of me?

5. Someone just asked you on your dream date. Where are they taking you?

6. What are three things you are looking for in a partner?

7. What makes you automatically swipe left on a person?

8. Have you ever experienced true love?

9. If you had a conversation with your ex, what’s a question you’d want to ask them?

10. What are your most frequently used emojis in text conversations?

11. What’s the wildest thing you’ve ever done to get someone’s attention?

12. What’s your biggest fear when it comes to relationships?

13. What’s the most embarrassing thing you’ve ever done in front of someone you like?

14. Do you find first dates fun or stressful?

15. What’s your favourite movie couple and why?

16. What’s your favourite place to take a significant other?

17. Whose relationship do you admire and why?

18. At what point in a relationship do you think it’s time to go public on social media?

19. What’s your biggest turn-on?

20. What’s your biggest turn-off?

21. What’s your favourite thing about me?

22. What was the last flirty text you sent?

23. What’s the worst thing about being single?

24. What’s the best thing about being single?

25. Would you consider yourself a hopeless romantic?

26. At this point in your life, would you prefer a casual relationship or a serious one?

27. What’s the hardest part about being in a long-term relationship?

28. You’re getting married tomorrow, and you have to have a themed wedding. What theme are you choosing?

29. What’s your biggest regret when it comes to a past relationship?

30. How do you get over a breakup?

31. What meme best represents your life?

32. Would you rather love and lose, or never love at all?

33. After a disagreement, do you initiate the makeup conversation or wait for your S.O. to?

34. How many people have you said “I love you” to in a romantic context?

35. What’s the silliest excuse you ever used to get out of a date?

36. What’s the most romantic thing someone has ever done for you?

37. What’s your favourite thing to do on a lazy Sunday?

38. If you could take me anywhere in the world right now, where would it be?

39. If you could cook any meal for me, what would it be?

40. What’s the most attractive quality someone can have?

41. How do you usually flirt with someone you like?

42. What’s the most romantic gesture you’ve ever made?

43. What’s your love language?

44. Who was your first celebrity crush?

45. What’s the most daring place you’ve ever kissed someone?

46. Have you ever had a dream about me?

47. What are your erogenous zones?

48. If we were to dance right now, what song would you choose?

49. What’s a technically non-sexual thing or quality that you secretly find super attractive?

50. What’s one thing you’d love to do together?

This article first appeared on teenvogue.com

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