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Deep questions to ask

Thoughtful questions about memories, values, fears and hopes, for late conversations with people you trust.

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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. What's the nicest thing a stranger has done for you?
2. What have you changed your mind about in the last few years?
3. What's the first thing you remember being proud of?
4. What place from your childhood no longer exists?
5. What were family dinners like in your house growing up?
6. What moment would you relive exactly as it happened?
7. Who believed in you before you'd done anything to earn it?
8. What were you sure about at twenty that you're less sure about now?
9. Which goodbye do you still think about?
10. What did you learn at your family's kitchen table that you still use?
11. What's the hardest thing you've ever had to say out loud?
12. What risk didn't you take that you still wonder about?
13. What would your grandparents be most surprised by in your life?
14. What kindness did you never get to say thank you for?
15. What were you afraid of as a child that you still feel a little of?
16. What did you have to learn the hard way?
17. What do you hope people say about you after you leave a room?
18. When did you first feel like an adult?
19. Where do you feel most like yourself?
20. Which of your parents' habits have you caught yourself repeating?
21. What promise did you make to yourself and keep?
22. What do you wish someone had told you at sixteen?
23. Who do you miss that you could still call?
24. What did you forgive that you didn't expect to?
25. What small moment changed the direction of your life?
26. What would you do with a year off and no one to answer to?
27. What are you proud of that you rarely get to mention?
28. What fear have you outgrown, and what replaced it?
29. What lesson do you keep having to relearn?
30. What did you once want badly and are now glad you didn't get?
31. What's the bravest thing you've seen someone else do?
32. What part of your younger self do you miss?
33. What does home mean to you now compared with ten years ago?
34. What question do you wish people asked you more often?
35. Which ordinary day from your past would you give a lot to have again?
36. Who shaped your idea of what a good person looks like?
37. What have you stopped apologizing for?
38. Which memory gets better every time you tell it?
39. What's the best mistake you ever made?
40. What would ten-year-old you think of your life today?
41. What do you want to be doing on an ordinary Tuesday ten years from now?
42. Which tradition do you want to pass on, and which one ends with you?
43. What compliment do you find hard to believe?
44. What's the longest you've held a grudge, and how did it end?
45. When did someone's honesty sting and help at the same time?
46. What do you know about friendship now that you didn't at eighteen?
47. What scares you about getting what you want?
48. Who would you most like to make proud, and why them?
49. What did you give up on that deserves another try?
50. What song can change your mood in ten seconds, and what's the memory behind it?
51. Where were you the last time you felt completely free?
52. What's the kindest thing you've done that nobody knows about?
53. What did you used to think about yourself that turned out to be wrong?
54. Which conversation changed how you see someone?
55. What do you think you'll be nostalgic for about right now?
56. What did your parents get right that you only noticed later?
57. When do you feel most understood?
58. Which closed door turned out to be a favor?
59. What would you like to be brave enough to try?
60. What book, film or song found you at exactly the right time?
61. What hard stretch are you now grateful for?
62. Which friend has changed you the most, and how?
63. What do you do when no one needs anything from you?
64. What do you want more of in your life, and what's in the way?
65. What do you wish you could tell someone who's no longer around?
66. What was the first big choice you made that was truly your own?
67. What moment made you realize your parents were just people?
68. What have you made that you hope outlasts you?
69. When were you last moved by a stranger?
70. Which regret taught you something useful?
71. What would you study if grades and careers didn't exist?
72. What do you find hard to ask for?
73. What beautiful thing did you see this week that most people walked past?
74. What's the most important thing an older person ever told you?
75. What object do you keep only because of the story behind it?
76. Which job, place or person did you leave at the right time?
77. When did you last do something for the first time?
78. What's the nicest thing a friend did for you that they've probably forgotten?
79. What am I better at than I give myself credit for?
80. When were you really proud of one of us?
81. How have I changed since we met?
82. When did you need a friend and one showed up?
83. What do you want us to still be doing together in twenty years?
84. When did you know we'd be friends for a long time?
85. What do you admire in a friend that you've never told them?
86. Which friendship did you lose that you still think about?
87. What's the kindest lie a friend has ever told you?
88. What's the best thing a friend ever talked you into?
89. What do you bring to a friendship that you're proud of?
90. When do you feel closest to me?
91. When were you proud to be with me?
92. What did you worry about at the start of us that turned out fine?
93. What would you like me to ask you about more often?
94. What dream of yours could I help with?
95. What's the scariest thing we've done together that we'd do again?
96. When did you first feel at home with me?
97. What about me took you a long time to understand?
98. What do you want us to be like at seventy?
99. When did you know you could count on me?
100. What did your parents do as a couple that you want for us?
101. What did you first notice about how I treat other people?
102. What do you admire about how I handle hard days?
103. What tells you early on that someone is worth your time?

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 deep questions to ask?

Five from this list: What were you sure about at twenty that you're less sure about now? What fear have you outgrown, and what replaced it? What did you give up on that deserves another try? Which regret taught you something useful? When do you feel closest to me?

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