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

Childhood (questions 1–20)

1. Where were you born and what was the house like?
2. What did your bedroom look like as a child?
3. Who was your closest friend when you were 8?
4. What chores did you have to do?
5. What did your mother smell like?
6. What was your favorite meal growing up?
7. What scared you the most as a kid?
8. What's a sound from your childhood you can still hear?
9. What did you wear to school?
10. What did your grandparents look like?
11. What was the first song you remember loving?
12. What did you want to be when you grew up?
13. What was the worst trouble you got into?
14. Who was your favorite teacher and why?
15. What was your family's Sunday routine?
16. What's a smell that takes you back to age 10?
17. What did your father do for work?
18. What was the hardest year of your childhood?
19. What was a holiday tradition that no longer exists?
20. What's something about your childhood you've never told anyone?

Young adulthood (questions 21–45)

21. How did you meet your first love?
22. What was your first job and what did you earn?
23. What did you wear on your first date with grandpa?
24. What were you doing the day you turned 18?
25. What did you think your life would look like at 30?
26. What was the bravest thing you did in your 20s?
27. What's a decision you remade in your head for years?
28. Who was the first person who broke your heart?
29. What was the first apartment like?
30. What music did you play when no one was home?
31. What did you fight with your parents about?
32. What did you believe at 22 that you no longer believe?
33. What did your wedding day actually feel like?
34. What did the world feel like in your 20s?
35. What's something you wish someone had told you?
36. What's a friend you lost touch with that you still think about?
37. What was your honeymoon like?
38. What was your first big argument with grandpa?
39. What was your dream for your children before they were born?
40. What did you not know about marriage?
41. What was the first big risk you took?
42. What's a moment from your 20s you'd live again?
43. What's a moment from your 20s you'd undo?
44. What did you do for fun before kids?
45. What was the bravest thing about becoming a mother?

Motherhood and middle years (46–70)

46. What was the day each of your children was born like?
47. What was the hardest part of being a young mother?
48. What did you learn from each of your children?
49. What did you wish you had done differently as a parent?
50. What's something only mothers know?
51. How did your marriage change after kids?
52. What's a sacrifice you made that no one noticed?
53. What was your proudest moment as a parent?
54. What did you miss most about being childless?
55. What did you fear most as your kids grew up?
56. What did you do when you needed a break?
57. What's a tradition you started for your family?
58. What was your hardest financial year?
59. What did you and grandpa argue about most?
60. What did you love most about your house when the kids were small?
61. What's a friend who saved you in those years?
62. What's something one of your kids said that you've never forgotten?
63. How did you handle losing your own parents?
64. What did you do when you were lonely?
65. What were you most afraid your kids would inherit from you?
66. What's a secret you've kept from your children?
67. What did you learn the hard way about money?
68. What did you give up that you don't regret?
69. What did you give up that you do regret?
70. What kept your marriage together through the hard parts?

Wisdom and reflection (71–100)

71. What do you know now that you wish you'd known at 25?
72. What's the kindest thing anyone ever did for you?
73. What do you want your great-grandchildren to know about you?
74. What's the best advice your mother ever gave you?
75. What's the best advice your father ever gave you?
76. What's a regret you've made peace with?
77. What's a regret you haven't made peace with?
78. Who is the person you most want to thank?
79. What do you believe about death?
80. What do you want at your funeral?
81. What's a possession you want a specific person to have and why?
82. What's a story about our family no one else knows?
83. What do you wish people understood about getting old?
84. What's the happiest you've ever been?
85. What's the saddest?
86. What's a song that should be played at my wedding?
87. What's a recipe you want me to learn?
88. What's the most important lesson you've learned about love?
89. What's the most important lesson about money?
90. What's the most important lesson about friendship?
91. What did your faith give you?
92. What did your faith fail to give you?
93. What do you hope is true after you die?
94. What would you tell your 20-year-old self?
95. What would you tell me when I'm your age?
96. What's a piece of your handwriting you want me to keep?
97. What's the most beautiful place you've ever been?
98. What's a small moment you think about often?
99. If you could send one message to your great-great-granddaughter, what would it be?
100. What's a question you wish I had asked sooner?

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