100 Questions to Ask Your Grandpa Before It's Too Late

Childhood and family (1–20)

1. Where were you born and what did the town look like?
2. What did your father do for work?
3. What did your mother do?
4. What was the smell of your childhood home?
5. What did you do for fun before TV?
6. What scared you most as a boy?
7. What was the worst trouble you got into?
8. What's a punishment you remember?
9. What did you want to be when you grew up?
10. What was your bedroom like?
11. What did your grandparents look like?
12. What did you eat on Sundays?
13. Who was your best friend at 10?
14. What did you have that kids today don't?
15. What did kids today have that you wish you'd had?
16. What did your father teach you?
17. What did your father never teach you?
18. What was your hardest year as a child?
19. What's a smell from age 8 you can still summon?
20. What's something about your childhood you've never told anyone?

Work, service, and young manhood (21–50)

21. What was your first job and how much did it pay?
22. What did you learn working for your first boss?
23. Did you serve in the military, and what was that like?
24. What was the hardest physical work you ever did?
25. What's a job you took just for the money?
26. What's a job you'd do again for free?
27. What did you think of America at 22?
28. What did you fight with your father about?
29. What did your mother worry about most?
30. How did you meet grandma?
31. What did you wear on your first date?
32. When did you know you'd marry her?
33. What was the first apartment like?
34. What did you fight about as newlyweds?
35. What did you not know about marriage?
36. What did your father teach you about being a husband?
37. What did you teach yourself?
38. What was the first big purchase you made?
39. What was the first time you felt like a man?
40. What was the scariest moment of your 20s?
41. What was the bravest?
42. What's a friend from those years you still miss?
43. What's a song that takes you back to 25?
44. What did the country feel like then?
45. What did you believe politically that you no longer believe?
46. What did you believe about God then?
47. What do you believe now?
48. What did you assume your life would look like?
49. What surprised you most about how it actually went?
50. What did you give up that you don't regret?

Career, fatherhood, and middle life (51–80)

51. What was the day each of your children was born like?
52. What kind of father did you want to be?
53. What kind do you think you were?
54. What did you learn from each child?
55. What did you wish you had done differently?
56. What's a moment with your kids you replay often?
57. What did you sacrifice for your family?
58. What did your work cost you?
59. What did you love about your work?
60. What did you hate?
61. What was your hardest financial year?
62. What did you and grandma argue about most?
63. What kept the marriage together?
64. What did you do when you needed to be alone?
65. What did you do for fun?
66. What was a friend who saved you?
67. What did you fear most as your kids grew?
68. What did you do when one of them disappointed you?
69. What did you do when you disappointed them?
70. What did you teach yourself about being a man?
71. What did your father get right that you copied?
72. What did he get wrong that you tried to undo?
73. What was your proudest moment as a father?
74. What's a secret you've kept from your kids?
75. What's a secret you've kept from grandma?
76. What's the kindest thing she ever did for you?
77. What did you do when you lost your own father?
78. What did you do when you lost your mother?
79. What's a friendship you let slip and regret?
80. What's a piece of advice you gave that someone followed?

Wisdom and legacy (81–100)

81. What do you know now that you wish you'd known at 25?
82. What's the best advice you ever got?
83. What's the worst?
84. What's the most important lesson about money?
85. About work?
86. About marriage?
87. About being a father?
88. About friendship?
89. About God?
90. About death?
91. What do you want at your funeral?
92. What possession do you want a specific person to have, and why?
93. What's a story about our family no one else knows?
94. What do you wish people understood about getting old?
95. When were you happiest?
96. When were you most afraid?
97. What do you want your great-grandchildren to know about you?
98. What would you tell your 20-year-old self in one sentence?
99. What would you tell me when I'm your age?
100. What's a question you wish I'd asked sooner?

Frequently asked questions