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Questions to ask your friends

Questions for friends you already know well, to find out the things you somehow never asked.

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How to use these questions

1. Choose a list that fits who you're talking to.
2. Take turns drawing a question. The person who draws it asks, and everyone else answers.
3. Ask one follow-up before moving on. The follow-up is usually where the good part is.

Updated November 2026.

1. Who's your oldest friend, and how did you two meet?
2. What are you proud of that you rarely get to mention?
3. What have you stopped apologizing for?
4. Which memory gets better every time you tell it?
5. What's the longest you've held a grudge, and how did it end?
6. What do you know about friendship now that you didn't at eighteen?
7. What did you give up on that deserves another try?
8. Which friend has changed you the most, and how?
9. What's the dumbest accident you've ever had?
10. What's the most ridiculous argument you've ever won?
11. What's the lamest excuse you've given for being late?
12. What would you be arrested for if being annoying were a crime?
13. What song do you know every word to and wish you didn't?
14. What's the least impressive thing you've ever bragged about?
15. What's the most pointless thing you've ever cried about?
16. What did you pretend to understand for far too long?
17. What's the longest you've kept a lie going about something tiny?
18. What's the most childish thing you still do?
19. What nickname do you hope never comes back?
20. What's the worst text you've ever sent to the wrong person?
21. What's the pettiest reason you've ever stopped liking someone?
22. What's the most elaborate plan you've made to avoid a small task?
23. What's your first memory of me?
24. What did you think of me before we became friends?
25. Which of us would last longest on a desert island, and who's out first?
26. What's the best night out we've ever had together?
27. What story about us do you tell other people?
28. Who in our group would you call first at 3 a.m. with a flat tire?
29. What do I do that you've quietly copied?
30. What's the worst idea we've ever had together?
31. Which friend of ours gives the best advice, and who gives the worst?
32. What have you never told me because it seemed too small to mention?
33. What's the hardest we've ever laughed together?
34. If our group were a sitcom, who would play which part?
35. Which habit of mine would you change if you could pick one?
36. What do you think I'll be like at eighty?
37. What's the nicest thing a friend did for you that they've probably forgotten?
38. Who in this group is most likely to end up famous, and for what?
39. When did I annoy you and you let it slide?
40. What's our best inside joke, and how did it start?
41. Which of us is the worst driver, and what's the proof?
42. What hidden talent does one of us have that deserves more attention?
43. What's the most trouble we've been in together?
44. What song will always make you think of our group?
45. What am I better at than I give myself credit for?
46. What job would each of us have in a heist?
47. When were you really proud of one of us?
48. What's the worst outfit you've ever seen me leave the house in?
49. Which of us would survive a horror movie, and who trips in the first scene?
50. What do we always say we'll do and never do?
51. What did we fight about that seems ridiculous now?
52. How have I changed since we met?
53. If we opened a business together, what would it be, and who gets fired first?
54. When did you need a friend and one showed up?
55. Which of us would be the strictest parent?
56. What rumor about you from school should I know?
57. What's your favorite detail about how we met?
58. Who in the group has the best taste in music, and who should never get the speaker?
59. What's the last thing one of us did that was completely in character?
60. What do you want us to still be doing together in twenty years?
61. Who takes longest to get ready, and who's always waiting in the car?
62. What's the most embarrassing thing you've seen me do?
63. What phase did one of us go through that we should never forget?
64. What have you borrowed from a friend and never returned?
65. When did you know we'd be friends for a long time?
66. What group tradition should we start this year?
67. Who's most likely to get us lost, and who gets us home?
68. What's the funniest moment of ours that nobody got on camera?
69. What do you admire in a friend that you've never told them?
70. Who's the worst cook in the group, and what's the evidence?
71. What do only your oldest friends know about you?
72. What's your role in this friend group, in your own words?
73. What do you think each of us was like at age eight?
74. Which friendship did you lose that you still think about?
75. What's the kindest lie a friend has ever told you?
76. Who here would you trust to plan your birthday, and who gets no say?
77. What bad decision did a friend talk you out of?
78. What's the best thing a friend ever talked you into?
79. What's the longest we've gone without talking, and who broke the silence?
80. Which of us would do best on a quiz show, and in what category?
81. What did you learn from a friend's family that yours never taught you?
82. What do you bring to a friendship that you're proud of?
83. What's the weirdest thing we both like?
84. What message from a friend made your whole week?
85. Who in the group is most likely to cry at a commercial?
86. What's your favorite memory with a friend from before you turned twelve?
87. What am I wrong about that you've stopped arguing over?
88. Which of us would you send to talk our way out of trouble?
89. What did one of us say years ago that we still quote?
90. What's the best thing we ever did with no budget and no plan?
91. What story would you tell in a toast about me?
92. Who was your first crush, and what did you do about it?

Tips for a better game

• Answer the question yourself too. People open up more when the asker goes first.
• Skip any card without explaining why. Nobody owes an answer.
• On a long drive or a quiet dinner, put the phone in the middle and let each person draw one.

Questions people ask

What are some good questions to ask your friends?

Five from this list: What did you give up on that deserves another try? Which of us would last longest on a desert island, and who's out first? What song will always make you think of our group? What's the most embarrassing thing you've seen me do? What did you learn from a friend's family that yours never taught you?

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