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72 Best Things To Ask When Playing 21 Questions

21 Questions might be the most all-purpose game ever created. Need an icebreaker? Perfect. Looking to learn more about your friends at your next sleepover? Fabulous. Want to keep the conversation flowing on a first date? Great. You can do all of those things by playing 21 Questions. And it’s free!

Below is a list of questions that can serve as the basis for your next game. They cover a wide range of topics and can tell you a lot about a person, so get ready to dig deep. Your answers can be as long or short as you want — as long as you tell the truth. Have fun!

1. What movie never fails to make you cry?

3. What is the most-worn item in your wardrobe?

4. Which mythical creature do you relate to on a spiritual level?

5. Who would you trust to help you bury a body?

6. What moment in your past do you wish you could experience again for the first time?

7. Which social media app do you use the most?

8. Which family member do you talk to the most?

9. What was your first kiss like?

10. What’s your wildest dating story?

11. Do you believe in astrology?

12. Do you believe in soulmates?

13. Do you believe in the concept of ‘The One’?

15. Do you think dating apps are a good way to meet someone?

16. What’s the most admirable trait a person can have?

17. What’s your go-to takeout order?

18. Do you have any weird secret habits?

19. What do you wear to sleep?

20. What keeps you up at night?

21. If you could go back and change your biggest mistake, would you?

22. What’s the worst lie you’ve ever told?

23. Would you ever go swimming with sharks?

24. Do you ignore red flags or bail at the first one?

25. What gives you the ick?

26. Do you like karaoke? If so, what’s your song?

27. What is the place you’d most like to visit?

28. How often do you shower?

29. What time do you like to wake up every day?

30. If you could compete in any Olympic sport, which one would you pick?

31. What’s your favorite cake flavor?

32. Do you stay calm during an emergency?

33. Do you prefer walking or driving?

34. How many tabs are currently open on your phone?

35. Is your room messy?

36. Are you an early bird or a night owl?

37. How many people’s birthdays do you know by heart?

38. How many phone numbers do you know by heart?

39. Would you consider getting married in Las Vegas by an Elvis impersonator?

40. Have you ever forgotten the name of someone you dated or hooked up with?

41. Would you ever wear matching outfits with your significant other?

42. Have you ever given someone a fake phone number?

43. Do you think six months is too soon to marry someone?

44. Have you ever shoplifted for the thrill of it?

45. What Guinness World Record do you think you’d have a shot at breaking?

46. Would you ever enter an eating contest?

47. Do you have any interest whatsoever in exploring space?

48. What celebrity are you certain you’d get along with?

49. Do you have any interest whatsoever in climbing Mount Everest?

50. Have you ever gotten kicked out of a bar or club?

51. Have you ever given yourself a haircut in a fit of rage?

52. What’s your favorite gift you’ve received?

53. Would you ever go completely off the grid for a year?

54. What is your ideal pet?

55. What is a story about yourself that you’ve told a million times?

56. Have you ever wanted to start a podcast?

57. What’s the best advice you’ve ever gotten?

58. What’s the story behind your most embarrassing accident or injury?

59. Do you still have any of your childhood stuffed animals?

60. What is your go-to recipe?

61. Have you ever been on the news?

62. Do you think you’d survive on a desert island?

63. Do you think you’d survive a zombie apocalypse?

64. How many unread texts and emails do you have?

65. Are you good at keeping secrets?

66. Do you have an idea for a business you want to start?

67. Do you like dad jokes?

68. Who is your favorite actor?

69. Have you ever been skinny dipping?

70. Are you usually the first or last person to leave a party?

71. Have you ever been in a physical fight?

72. Are you better at telling lies or spotting them?

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