The Ultimate Sleepover Questions for Girls' Night

The best sleepovers I have ever had did not involve a plan.

They involved the specific hour that happens after midnight when everyone has run out of the version of themselves they perform in public and has become just the actual person.

Nobody is trying to say the right thing anymore.

The conversation goes somewhere it would not have gone at dinner.

Someone says something honest and everyone else says me too and the whole room shifts.

These 100 questions are for that hour.

Some of them are ridiculous and some of them are the kind of thing you have been wanting to say for months and never quite found the right moment for.

Go through them however you want.

Pick one out of order.

Answer the ones that make everyone go quiet for a second.

Those are always the best ones.

100 Girl Talk Questions for Your Next Sleepover

I.  The Fun and Ridiculous Ones

Start here. You need to warm up before anyone is willing to say anything real.

1. If your life had a theme song that played whenever you walked into a room, what would it be?

2. What is the most embarrassing thing you have ever done in front of someone you wanted to impress?

3. What is your most irrational fear that you are slightly ashamed of?

4. What is the most dramatic thing you have ever done after a breakup?

5. What is the worst fashion decision you ever committed to fully?

6. What is a lie you told as a child that somehow never got found out?

7. What is your most embarrassing autocorrect or wrong person text story?

8. If you had to describe yourself using only a Kardashian, which one and why?

9. What is the most questionable thing you have eaten when you thought nobody was watching?

10. What is your most embarrassing celebrity crush, past or present?

11. What is the weirdest thing you have ever done when you were completely alone?

12. What is the most embarrassing thing you have done while drunk that you still think about?

13. If your personality were a type of cheese, what would it be and why?

14. What is something you did as a teenager that your parents still do not know about?

15. What is your most embarrassing gym or exercise story?

16. What is a completely useless skill you have that you are secretly proud of?

17. What is the worst date you have ever been on?

18. What is your most unhinged late night purchase?

19. What fictional character do you relate to most, and is that concerning?

20. What is something you genuinely believed as a child that turned out to be completely wrong?

II. Would You Rather

These are for when you need something with no wrong answer and a lot of debate.

21. Would you rather know the date you die or how you die?

22. Would you rather be famous for something embarrassing or completely anonymous forever?

23. Would you rather have your search history read out loud to your family or your texts from the last year?

24. Would you rather be able to read minds but never be able to turn it off, or be completely unreadable to everyone forever?

25. Would you rather relive your most embarrassing moment once a year or forget your ten best memories?

26. Would you rather be loved by someone you do not love, or love someone who does not love you back?

27. Would you rather always say exactly what you think with no filter, or never be able to say what you actually mean?

28. Would you rather have one really close friend or a huge group of people who all like you?

29. Would you rather know every language or be able to play every instrument?

30. Would you rather go back to being fifteen knowing what you know now, or skip ahead to fifty and see how things turned out?

III. Hot Takes and Controversial Opinions

These will either end in someone slamming their hand on the table or make everyone realise they have been thinking the same thing.

31. What is something everyone around you seems to love that you genuinely do not get?

32. What is your most controversial opinion about something completely low-stakes?

33. What is a common life advice cliché that you actually think is wrong?

34. What is your honest opinion about astrology and do you secretly check your horoscope?

35. What is a popular film or show that you think is genuinely overrated?

36. What is something that is considered a red flag that you actually find endearing?

37. What is something that is considered a green flag that you think is actually overrated?

38. What is your genuinely unpopular opinion about something in the friend group?

39. What is a double standard you have noticed that nobody seems to talk about?

40. What is something you changed your mind about completely that you used to feel strongly about?

IV. Boys, Dating, and All That

The sleepover classics.

41. What is your absolute non-negotiable dealbreaker in a relationship?

42. What is something you have done in a relationship that you are slightly ashamed of?

43. What is the most confusing thing a guy has ever done and what did you convince yourself it meant?

44. What is your honest opinion on situationships and have you ever been in one?

45. What is the most embarrassing thing you have done while trying to seem unbothered?

46. What is something you did for a relationship that you would never do again?

47. What is the one that got away and do you think about them?

48. What is something a partner has said or done that you have never told anyone?

49. What is your biggest ick — the one that immediately ends any attraction no matter who it is?

50. What is something you need in a relationship that you have never been able to ask for directly?

V. Getting Real About Life

After the giggling has settled and everyone has run out of snacks, this is where it gets interesting.

51. What is something you are genuinely proud of from this year that you have not told many people?

52. What is something you thought you would have figured out by now that you are still working on?

53. What is a version of yourself you have been trying to move away from?

54. What is something you want more of in your daily life right now?

55. What is the hardest thing you have had to do in the last few years?

56. What is something you have changed your mind about in the last year?

57. What is a goal you have quietly given up on, and do you regret it?

58. What is something you have been putting off that you know you need to do?

59. What do you think is the most important thing you have learned in your twenties so far?

60. What does your dream life actually look like — the honest version, not the one that sounds good?

VI. Friendship Questions

The ones about each other and what you mean to each other.

61. What is something you love about this friend group that you do not say enough?

62. What is something another person in this room has done that genuinely impressed you?

63. Who in this group would survive the longest in a survival situation and what is your reasoning?

64. What is something you wish you had said to someone in this room but kept talking yourself out of?

65. Who in this group would you call first if something went really wrong?

66. What is something you appreciate about each person here that you have never directly said?

67. Who in this group has changed the most since you first met and in what way?

68. What is a memory with someone in this room that you genuinely treasure?

69. What is something you think one of your friends deserves more credit for?

70. What would you want this friend group to look like in ten years?

VII. Never Have I Ever

You know how this works. Hold up a hand.

71. Never have I ever pretended not to see someone in public to avoid talking to them.

72. Never have I ever stalked an ex’s social media after telling everyone I was completely over it.

73. Never have I ever laughed at something I absolutely should not have laughed at.

74. Never have I ever sent a message and then desperately wished I could unsend it.

75. Never have I ever made a decision because I wanted to make someone else jealous.

76. Never have I ever cried at something embarrassing and told nobody.

77. Never have I ever liked a photo from years back on someone’s Instagram by accident.

78. Never have I ever been the reason for a piece of gossip.

79. Never have I ever cancelled plans and then felt completely fine about it immediately.

80. Never have I ever googled an ex’s name at a low moment.

VIII. The Deep End

Save these for when it is genuinely late and someone has already said one honest thing and the room has gotten quieter.

81. What is something you have never said to anyone that you have been carrying for a while?

82. What is your biggest fear — not a physical thing, the internal one?

83. What is something you have forgiven someone for that took longer than people might expect?

84. What do you think is the thing people most misunderstand about you?

85. Is there something you have been pretending is fine when it is not?

86. What is a relationship in your life — not romantic — that has shaped who you are most?

87. What is something you want that you have not let yourself want out loud yet?

88. What is the kindest thing anyone has ever done for you?

89. What is something about yourself that took you a long time to accept?

90. If you could change one decision from the last five years, would you, and what would it be?

IX. The Last Ones

These are for when everyone is horizontal and half asleep and someone asks something and nobody feels like they need to perform an answer.

91. What is something you want to do before the end of this year?

92. What are you most grateful for right now, specifically?

93. What does a genuinely good day look like for you?

94. What is something you wish you had been told earlier?

95. What is one thing about yourself that has genuinely changed for the better?

96. What are you most looking forward to in the next year?

97. What is something you would tell your younger self?

98. Who in your life makes you feel most like yourself?

99. What is one thing you want more of in your friendships?

100. What is something you want the people in this room to know?

The questions you end up remembering from a sleepover are never the ones you planned.

They are the ones someone asked and then everyone went quiet and then someone answered honestly and then everyone did.

Pick a few. Start somewhere. Let it go where it wants to go.

The best conversations are the ones that surprised you.