I grew up in a multigenerational household, where my parents worked full time and my paternal grandparents helped raise me. And having that time together in the first decade and a half of my life? It’s among the memories I most cherish.

“I would give nearly anything to have one final conversation with them.”

Unfortunately, I was only 13 years old by the time both grandparents passed away—and in the time we did share, I didn’t think to ask them more about their lived experiences. To this day, it is one of my deepest regrets, and I would give nearly anything to have one final conversation with them. To hear their final hopes and dreams, to understand their lives beyond just “being grandparents,” to know how they’d like their legacies carried on.

If you are lucky enough to have a positive relationship with your grandparents and they are still around, I encourage you to ask some of the 99 questions below. You can also transcribe their answers like I am doing now with my parents, or journal through a question each time you’re together. You’ll learn more about them, your family, and yourself along the way.  💕

1. Which of your childhood memories was most meaningful?

2. Can we make your favorite meal together, or do you have a recipe you can share?

3. What was your life like before having children? In which ways did it change?

4. What brings you the most joy right now? What about as a child?

“Are there any experiences on your bucket list? Can we do them together?”

5. Are there any experiences on your bucket list? Can we do them together?

6. Is there anything you’d change in your life now?

7. What advice or wisdom would you like to impart for future generations?

8. Can I hear more about your greatest love story—whether with a person, a place, or a pet?

9. What do you hope for in the future? What about the future of our planet or of society?

10. What do you wish someone had done for you at X time in your life?

11. If you could do it all over again, would you choose a different path or career?

12. Is there a book or movie that changed your life? Why?

“Which cultural traditions would you like me to preserve?”

13. Which cultural traditions would you like me to preserve?

14. Why was it so important for you to do X (i.e., move away from home, take a specific role, walk away from a relationship)?

15. How would you define the happiest moments of your life?

16. What were the biggest challenges? What did you learn from them?

17. What was your favorite class in school? What about your least favorite? How did that influence your life?

“How did you spend your free time as a child?”

18. How did you spend your free time as a child or young adult?

19. Which sibling (or family member) did you spend the most time with, and why?

20. What was your favorite outfit? Could we recreate a similar version today?

21. What is the most sentimental heirloom you own? What meaning does it hold?

22. Out of all the holidays, which one do you most enjoy celebrating?

23. How did you choose your children’s names? How do you feel about your own name?

“Which traits do you most love and respect about yourself?”

24. Which childhood toys or games brought you joy?

25. Tell me about the experience you’re most proud of.

26. Which traits do you most love and respect about yourself?

27. How would you describe the most difficult and rewarding parts about being a parent?

28. So many important historical events have happened over your lifetime—which ones stand out in your memory?

“Which health problems run in our family?”

29. Which health problems run in our family? What should I look for that might be considered hereditary?

30. Can you tell me about your best friend (or longest friendship/relationship)?

31. If you could learn a new skill today, which would you pick? Would you pick up an old hobby?

32. What is the scariest thing that ever happened to you? How do you feel now about it?

33. In all your travels, which destinations have stuck with you the longest? Where have you gone that felt most special?

“What was the most peaceful moment of your life?”

34. What was the most peaceful moment of your life?

35. Do you have any moments you thought you might regret, but you don’t?

36. What do you wish you made more time for?

“Do you have any moments you thought you might regret, but you don’t?”

37. What is your favorite aspect of being a grandparent?

38. What song transports you back to being a teenager?

39. Is there a scent that gives you instant nostalgia?

40. Who is/was the most X (i.e., selfless, humorous, mischievous) person you know?

41. Can you share more about our family name and its origins?

42. What were my parents like when they were young? What were their lives like before I was born?

43. How have you experienced romance throughout your life?

44. Which songs or bedtime stories did you love hearing as a kid?

45. What was it like where you grew up? Can you describe the neighborhood in detail?

46. Which communities—formal or informal—have you been a proud member of, over the years?

“Which values do you hope you’ve embodied in your life?”

47. Which values do you hope you’ve embodied in your life? 

48. What has your relationship with money looked like? How has it evolved?

49. What is the most meaningful present someone could gift you today?

“What should your celebration of life look like when you’re gone?”

50. What should your celebration of life look like when you’re gone?

51. Can you describe your perfect weekend?

52. What has given you your confidence?

53. Which piece of media do you feel most represented or “seen” in: a timely play, an old-school movie, a thoughtful poem?

54. Which age (or life stage) was your favorite?

55. Tell me about your first X (i.e., date, car, home, book you remember reading).

56. Which humanitarian causes have you cared most about? How can I support them, too?

57. Who do you think was the funniest comedian of your generation? Or the most brilliant actor/actress?

58. What do you wish people knew about life back when you were young?

59. How do you feel about X (i.e., a current trend, a popular political issue, a new invention)?

“What do you miss most about your parents or grandparents?”

60. What do you miss most about your parents or grandparents?

61. Which home that you’ve lived in do you miss most? What felt most like home to you?

62. Who was your biggest role model, and why?

63. What did a typical day look like in your household, whether as a child or adult?

64. Who were the oldest people you knew growing up? What did you learn from them?

“Tell me about a time you laughed so hard you cried.”

65. Tell me about a time you laughed so hard you cried.

66. Which photograph(s) will you treasure forever?

67. Did you have any chores as a kid? Do you hate or love doing it now?

68. What would you say is the key to X (i.e., a successful marriage, a long-term friendship, being the best parent you can be, etc.)?

69. What was your most embarrassing moment?

70. Which long-lost family meal, sentimental beverage, or discontinued snack food would you love to have just one more time?

“Which long-lost family meal, sentimental beverage, or discontinued snack food would you love to have just one more time?”

71. Was there a habit you wished you’d quit earlier?

72. What did you say “no” to that you’re proud of?

73. What was your everyday beauty routine (i.e., hair, skincare, makeup, hygiene)?

74. If you could go back in time, what would you tell your 25-year-old self?

75. What were your childhood nicknames?

76. Can I hear more about your first date?

77. Tell me about your favorite family vacation.

78. Have you ever had a unique or unusual job?

“What do you wish you’d accepted about yourself earlier in life?”

79. What do you wish you’d accepted about yourself earlier in life?

80. At what age did you really feel like an adult or that you were all grown up?

81. What was your best or favorite haircut/style?

82. How did your own relationship with your grandparents evolve over the years?

83. Did your parents ever catch you doing something sneaky?

84. When was the first time you experienced grief?

85. Which teacher influenced you most, and in what ways?

86. What’s the best decision you think you’ve made over the years?

87. What about your biggest failure?

“Of all the lessons your parents instilled in you, which ones feel most valuable?”

88. Of all the lessons your parents instilled in you, which ones feel most valuable?

89. Is there a city or country you wish you could go to that you haven’t already?

90. What’s the earliest memory you can recollect?

91. How have your spiritual beliefs or faith changed over time?

92. When was the most peaceful time period—whether a few minutes or an entire decade—in your life?

93. Did you ever collect anything (toys, rocks, coins)? Do you still have that collection today?

“What’s your favorite memory of us spending time together?”

94. What’s your favorite memory of us spending time together?

95. Tell me about the most courageous thing you did.

96. Is there anything about our family tree I should know about?

97. If you could relive one decade of your life, which one would you choose and why?

98. Which part of getting older has been your favorite?

99. What do you wish I’d ask you?

Henah Velez (she/her) is the Senior Editor at Money with Katie at Morning Brew, as well as a writer at The Good Trade. She holds a Master’s in Social Entrepreneurship and is a proud Rutgers grad. Originally from NJ, Henah’s now in the Bay Area where she loves shopping small, hanging with her pets, or traveling.