75 Meaningful Questions to Ask Your Dad

His life before you (1–25)

1. What was your father like?
2. What was your mother like?
3. What did your father do for work, and how did he feel about it?
4. What did you do for fun before screens?
5. What scared you most as a kid?
6. What was the worst trouble you got into?
7. Who was your best friend at 12?
8. What did you want to be?
9. What did you think you'd be like as an adult?
10. What was your first job?
11. What did you spend your first paycheck on?
12. What did 18 feel like?
13. Did you serve in the military, and what was that like?
14. What's a friend from your 20s you still think about?
15. What was the bravest thing you did before 25?
16. What's a decision you nearly made that would have changed everything?
17. Who was the love before mom?
18. How did you meet mom?
19. What did you think on the first date?
20. When did you know?
21. What was the first apartment like?
22. What did you fight about as newlyweds?
23. What did you not know about marriage?
24. What did your father teach you about being a husband?
25. What did you have to teach yourself?

Work and fatherhood (26–55)

26. What was the day I was born like for you?
27. What kind of father did you want to be?
28. What kind do you think you were?
29. What did you learn from being my father that you didn't expect?
30. What did you sacrifice for the family that no one saw?
31. What did you love about your work?
32. What did you hate?
33. What was your hardest financial year?
34. What's a job you regret taking?
35. What's a job you wish you'd taken?
36. What did your father get right that you copied?
37. What did he get wrong that you tried to undo?
38. What did you fight with mom about most?
39. What kept the marriage together?
40. What did you do when you needed to be alone?
41. What did you do for fun?
42. What's a friend who saved you?
43. What was your proudest moment as a father?
44. What's a moment with me you replay often?
45. What's something I did that hurt you?
46. What's something I did that made you proud?
47. What did you teach me on purpose?
48. What did I learn from you that you didn't mean to teach?
49. What did you wish you'd taught me sooner?
50. What's a part of your story you never told me?
51. What did you do when you lost your own father?
52. What did you do when you lost your mother?
53. What's a friendship you let slip and regret?
54. What's a piece of advice you gave that someone followed?
55. What's the most important lesson about being a man?

Wisdom and legacy (56–75)

56. What do you know now that you wish you'd known at 30?
57. What's the best advice you ever got?
58. The worst?
59. What's the most important lesson about money?
60. About work?
61. About marriage?
62. About friendship?
63. About God?
64. About death?
65. What's a regret you've made peace with?
66. What's one you haven't?
67. What's a story about our family I don't know?
68. When were you happiest?
69. When were you most afraid?
70. What's the kindest thing anyone ever did for you?
71. What do you want at your funeral?
72. What possession do you want a specific person to have, and why?
73. What would you tell your 20-year-old self?
74. What would you tell me when I'm your age?
75. What's a question you wish I'd asked sooner?

Frequently asked questions