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

My grandfather passed away when I was 22. I was at his bedside in those final weeks, and I kept thinking: I never asked him about Korea. I never asked him why he left the farm. I never asked him what he was like before he was my grandfather.

I had his whole life sitting right there, and I waited too long to ask.

Most of us do. We assume the stories will always be there — that there will be another Sunday dinner, another holiday, another long phone call. And then, one day, there isn't. Not because we didn't love them. But because we didn't realize how little time we actually had.

These 100 questions to ask your grandparents are organized so you can work through them naturally — a few at a time, over many conversations. You don't have to ask all of them. You just have to start.

Childhood & Growing Up (Questions 1–15)

1. What is your very first memory?
2. Where did you grow up, and what was it like?
3. What did your childhood home look like inside?
4. What were your parents like when you were young?
5. Did you have siblings? What was your relationship like with them?
6. What were your favorite games or things to do as a child?
7. What did your neighborhood look like? Who were your neighbors?
8. What was your best subject in school? Your worst?
9. Who was your favorite teacher, and why?
10. What were your chores growing up? Did you get paid for them?
11. What did you eat for dinner most nights as a child?
12. What holidays did your family celebrate, and how?
13. What was the most mischievous thing you ever did as a kid?
14. Did you have a pet growing up? Tell me about it.
15. What did you want to be when you grew up?

Love & Relationships (Questions 16–25)

16. How did you meet Grandma/Grandpa?
17. What did you think of them the first time you met?
18. What was your first date like?
19. How did you know they were the one?
20. What was your wedding day like? What do you remember most?
21. What has been the secret to your marriage?
22. Did you ever have your heart broken? What happened?
23. Who was your best friend growing up, and what happened to them?
24. Is there a friendship from your life that you wish you'd maintained?
25. What advice would you give someone who is falling in love?

Work & Career (Questions 26–35)

26. What was your very first job? How old were you?
27. What job are you most proud of having done?
28. Did you ever have a boss who changed how you thought about work?
29. What did a typical workday look like for you?
30. Was there a career path you almost took but didn't?
31. What was the hardest professional decision you ever made?
32. Did you ever feel like you weren't being treated fairly at work?
33. What's the best piece of career advice you ever received?
34. What did you learn from the worst job you ever had?
35. If you could have had any job in the world, what would it have been?

Family & Raising Kids (Questions 36–50)

36. What was it like when your first child was born?
37. What was your parenting philosophy? Where did it come from?
38. What's something your parents did that you made sure to do differently?
39. What's something they did that you tried to carry forward?
40. What was the funniest thing one of your kids ever did?
41. What was the hardest part of raising children?
42. Was there a time you weren't sure you were doing the right thing as a parent?
43. What do you remember about the house or apartment where you raised us?
44. What did your family do for fun together?
45. Did you have a family tradition that you loved?
46. What's a family story that gets told at every reunion?
47. Who in the family is most like you, and in what way?
48. What did you sacrifice for your family that you never talked about?
49. What's something your children did that made you realize you'd done something right?
50. What do you most want your grandchildren to know about you?

Hard Times & Resilience (Questions 51–62)

51. What was the hardest period of your life?
52. How did you get through it?
53. Has there been a loss that still stays with you?
54. Did you ever experience something you thought you wouldn't survive?
55. What historical event affected your life the most personally?
56. Were there times when money was very tight? How did you manage?
57. Did you ever have to make a decision under real pressure? What happened?
58. Was there a time you failed at something important to you?
59. Did you ever face discrimination or unfairness? How did you handle it?
60. What helped you keep going when things were very hard?
61. Is there something difficult from your past that you've made peace with?
62. What has your faith, or your lack of it, meant to you during hard times?

Values & Life Lessons (Questions 63–75)

63. What do you believe in most deeply?
64. What's something you know now that you wish you'd understood at 25?
65. What's a piece of advice you were given that turned out to be wrong?
66. What's a piece of advice you were given that turned out to be right?
67. What does a good life look like to you?
68. What has been your greatest teacher?
69. What does money mean to you? How has that changed over time?
70. What do you think people get wrong about happiness?
71. Is there something you believe that most people around you don't?
72. What's the most important thing you've ever learned about people?
73. What do you think makes a good friend?
74. What qualities do you admire most in a person?
75. What has kindness looked like in your life — giving and receiving it?

Hopes & Regrets (Questions 76–85)

76. Is there something you always meant to do but never did?
77. Is there a place you always wanted to visit?
78. What's something you'd do differently if you could?
79. What decision are you most at peace with?
80. Is there a relationship you wish you'd handled differently?
81. What were you most afraid of at different points in your life?
82. What do you think your younger self would be surprised by?
83. What has surprised you most about getting older?
84. What do you still hope for?
85. If you could send a letter back to yourself at 20, what would it say?

Legacy & What They Want Remembered (Questions 86–100)

86. What do you want people to say about you when you're gone?
87. What's the most important thing you've contributed to this world?
88. What do you want your grandchildren to carry forward from your life?
89. Is there a story from your life that you've never told anyone?
90. What's a part of your history that might be lost if you don't share it?
91. Who in your life deserves more credit than they got?
92. What are you most proud of?
93. What has brought you the most joy?
94. Who has loved you most in your life, and how did they show it?
95. Who have you loved most?
96. What does home mean to you?
97. If your life were a book, what would the title be?
98. What do you think happens after we die?
99. What has your life meant, in your own words?
100. Is there anything you want to make sure I know — anything at all?

The hardest part isn't the questions — it's actually doing it

You've read through 100 questions to ask your grandparents. Some of them probably stopped you for a moment. Some you can already imagine the answer to. Some you realize you have no idea what they'd say.

That last group — that's where the real work is. Those are the stories that exist only in the minds of the people who lived them, and the window to capture them is smaller than it feels.

The hard truth is that most people never actually do these interviews. Not because they don't want to. Because it requires coordination — finding the right moment, sitting down with intention, asking the awkward follow-up. Life gets in the way. The next visit becomes next month. Next month becomes next year. And then, one morning, you realize the chance is gone.

That's why we built Memoora. Lila, our AI story guide, calls your grandparent or parent weekly — on their regular phone, no app required — and asks them questions exactly like these. The conversations are recorded and transcribed automatically. You get to listen to their voice telling stories you might never have thought to ask about. The whole family can access them, share them, and keep them forever.

You don't have to coordinate it. You don't have to remember to call. You just have to start — and we'll do the rest.