Everyone has played a Truth or Dare game sometime in life. It probably happened at a junior high party and evolved into college shenanigans. Now that the post-college workforce has called, such games may have become a thing of the past. But do they have to? Perhaps a circle of friends is looking for a new pastime for a girls’ night. Well, look no further because we have gathered together 100 Truth or Drink Questions that remove the fear of dares and help you get to know your friends on that next level.

How to Play Truth or Drink

It’s simple, really. Just like in the games of the past, players either answer a question truthfully or elect to drink. Now, the drinks can be determined at the outset of the game. Players can choose to use beer or liquor, and the amount should be determined as well. Shot glasses are always a good choice for the game as they can be used to measure the same amount of alcohol or beer for each round. If liquor is used, just a word of caution … the game may be short-lived. But, perhaps that’s the fun of it.

Without further ado, here are 100 questions for a game of Truth or Drink. Use them to get to know your friends in an even deeper and more fun way.

Truth or Drink Questions About Sex & Intimacy

Let’s just cut straight to it. These are the questions most people want to jump to from the get-go (at least when it comes to reading up on Truth or Drink Questions). However, if players want to make it a real fun game, reserve these questions for the midway point. That way, a few rounds of alcohol have been imbibed, players are loosened up and ready to share!

The Number One Question: What’s your most awkward sexual encounter?

2. Have you ever had a romantic encounter with someone much older or younger?

3. Share a sexual fantasy you’ve never told anyone about.

4. What’s the most embarrassing thing that happened during sex?

5. Have you ever had a crush on a friend’s significant other? What did you do?

6. What’s the weirdest place you’ve ever been intimate with someone?

7. Have you ever had a friends-with-benefits arrangement? How did it turn out?

8. Share a story of a sexual mishap that still makes you cringe.

9. What’s your favorite and least favorite thing about your sex life?

10. If you could change one thing about your sexual history, what would it be?

Wild and Wacky

11. Have you ever been caught doing something you shouldn’t be doing?

12. What’s the weirdest food combination you enjoy?

13. What’s the craziest thing you’ve done under the influence of alcohol?

14. Have you ever had a paranormal or supernatural experience?

15. If you had to join a circus, which act would you perform?

16. What’s the strangest rumor you’ve heard about yourself?

17. Have you ever shoplifted or stolen something? What was it?

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

19. Have you ever had a near-death experience? What happened?

20. What’s the silliest fear you have that most people find ridiculous?

Regrets and Guilty Pleasures

21. What’s the one thing you regret doing or not doing in your past?

22. Share a guilty pleasure that you’ve never admitted to anyone.

23. Have you ever said “I love you” without meaning it?

24. What’s the most embarrassing thing you’ve cried about?

25. Have you ever ruined someone else’s relationship? How?

26. What’s the biggest lie you’ve told your parents as an adult?

27. Have you ever stolen something from a friend? Did they find out?

28. What’s the most expensive item you’ve regretted purchasing?

29. Have you ever spread a rumor about someone? What was it?

30. What’s the most selfish thing you’ve done in the past year?

Getting to Know Each Other

31. What’s the most embarrassing thing you’ve ever done while intoxicated?

32. Have you ever had a crush on someone in this group? Who?

33. What’s your wildest fantasy that you’ve never shared with anyone?

34. If you could switch lives with anyone here for a day, who would it be and why?

35. What’s the most illegal thing you’ve ever done?

36. Have you ever had a one-night stand? Details!

37. What’s the weirdest thing you find attractive in a person?

38. If you had to date someone from this group, who would it be and why?

39. What’s the most embarrassing thing you’ve searched for on the internet?

40. Have you ever had a romantic dream about someone in this group?

Relationships and Love

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

42. Have you ever cheated or been cheated on? Explain the situation.

43. What’s your biggest turn-off in a partner?

44. Have you ever been in love with someone who didn’t love you back?

45. What’s your most awkward dating experience?

46. What’s the longest you’ve gone without intimacy or sex?

47. Have you ever ghosted someone or been ghosted? Why?

48. Describe your ideal romantic partner in three words.

49. What’s the most spontaneous romantic thing you’ve ever done for someone?

50. What’s the most important quality you look for in a long-term partner?

Work and Career

51. Have you ever lied on your resume or during a job interview? What about?

52. What’s the most embarrassing thing that has happened to you at work?

53. Have you ever had a crush on a colleague? Did anything happen?

54. What’s the biggest mistake you’ve made at work?

55. If you could switch careers with someone here, who would it be and why?

56. Have you ever had a workplace romance? How did it end?

57. What’s the most inappropriate thing you’ve done during work hours?

58. Have you ever taken credit for someone else’s work? What was it?

59. What’s the most awkward encounter you’ve had with a coworker outside of work?

60. If you could fire one person from your current workplace, who would it be?

Travel and Adventures

61. What’s the worst vacation you’ve ever been on? Why?

62. Have you ever gotten into trouble with the law while traveling?

63. What’s the most adventurous thing you’ve done in a foreign country?

64. Share a travel story that you’ve never told anyone before.

65. Have you ever gotten lost in a foreign city? How did you find your way back?

66. What’s the most embarrassing cultural misunderstanding you’ve had while traveling?

67. Have you ever had a holiday romance? Tell us about it.

68. What’s the scariest experience you’ve had while traveling?

69. If you could live in any country for a year, where would you choose and why?

70. What’s the strangest food you’ve ever tried while traveling?

Personal and Deep

71. If you had one week left to live, what would you do?

72. What’s the biggest fear that keeps you up at night?

73. Share a secret that you’ve never told anyone, until now.

74. Have you ever had a life-changing realization? What was it?

75. What’s the most emotional song or movie for you? Why?

76. If you could apologize to someone from your past, who would it be and why?

77. Share a childhood memory that significantly impacted your life.

78. What’s the most difficult goodbye you’ve had to say?

79. Have you ever experienced unrequited love? Explain.

80. What’s the one thing you wish people understood about you?

Family Matters

81. What’s the biggest lie you’ve told your family?

82. Have you ever kept a significant relationship secret from your family? Why?

83. What’s the worst thing you’ve ever said to a family member?

84. Have you ever stolen money from your parents or siblings?

85. What’s the most embarrassing thing your family caught you doing?

86. If you could change one thing about your family, what would it be?

87. Have you ever been caught sneaking out of the house? What happened?

88. What’s the most rebellious thing you did as a teenager?

89. Share a family tradition that you secretly dislike.

90. Have you ever had a major disagreement with your parents? About what?

Social and Peer Pressure

91. Have you ever pretended to like something just to fit in with a group?

92. What’s the most ridiculous dare you’ve accepted?

93. Share a story of how peer pressure influenced a bad decision.

94. Have you ever participated in a protest or demonstration? What was it for?

95. What’s the most embarrassing thing you’ve done to impress someone?

96. Have you ever unfollowed or blocked someone on social media? Why?

97. What’s the biggest lie you’ve told to gain someone’s approval?

98. Have you ever done something illegal because someone pressured you to?

99. Share a story of a time when you stood up against peer pressure.

100. What’s the most embarrassing thing you’ve posted on social media?