74 questions to ask your grandparents about their life story

Grandparents carry decades of perspective. These prompts help you capture their stories in detail, honour their resilience, and understand the cultural context that shaped your family. Use them alongside the interviewing guidance in how to interview a relative and the archival tips in the cultural heritage story workbook.

Set up the conversation

• Let them know how you plan to use the stories and who will hear them.
• Choose a time when they feel rested and comfortable; short sessions often work best.
• Bring sensory anchors—photos, recipes, letters—to jog memories.
• Keep a glass of water, tissues, and breaks within reach.
• Record with permission and label every file right away.

Childhood and family roots

1. Where were you born, and what do you remember about the place?
2. How did your parents or caregivers meet?
3. What was your home like—decor, layout, smells, sounds?
4. Who lived with you growing up (siblings, grandparents, boarders)?
5. What chores did you handle, and which ones did you avoid?
6. What games or outdoor adventures filled your days?
7. Which family stories were told over and over?
8. How did your family celebrate milestones or holidays?
9. Who in the family gave the best advice?
10. What was your favourite meal, and who cooked it?

School and learning

11. How far did you travel to attend school?
12. Which teacher made you feel seen, and what did they do?
13. What subjects did you love or dread?
14. How did you pay for school supplies or uniforms?
15. What books, songs, or plays influenced you?
16. Did you ever skip school? What happened afterward?
17. How did classmates describe you?
18. What role did education play in your family’s expectations?
19. Did you speak multiple languages at school or home?
20. What was graduation (or leaving school early) like for you?

Community and culture

21. Where did people gather for gossip, news, or celebration?
22. Which community leaders or elders shaped local life?
23. How did your hometown change while you were growing up?
24. What local traditions—parades, festivals, rituals—stood out?
25. How did your family engage with faith, spirituality, or activism?
26. Who protected the neighbourhood during tough times?
27. When did you first feel responsible for others outside your family?
28. What gestures signalled respect or belonging in your culture?
29. Were there moments when you felt like an outsider? How did you respond?
30. What songs or sounds instantly carry you back to that community?

Work and purpose

31. What was your first paid job, and how did you land it?
32. How did you spend your first paycheque?
33. What unpaid labour (caregiving, farm work, volunteer roles) filled your time?
34. Did you ever start a business or side hustle?
35. Who mentored you in your early career?
36. What workplace victories make you proud?
37. How did you balance work with family responsibilities?
38. Did you face discrimination or barriers? How did you handle them?
39. What skills did you learn later in life that surprised you?
40. When did you decide to retire or shift gears?

Love and partnership

41. How did you meet your partner, and what was your first impression?
42. What did dating look like in your era?
43. How did you decide to build a life together?
44. What traditions did you start as a couple?
45. How did you resolve disagreements?
46. Who supported your relationship when times were tough?
47. What advice would you give younger couples today?
48. If you lost a partner, how did you honour their memory?

Parenting and family life

49. What surprised you about becoming a parent or guardian?
50. How did you handle sleepless nights or hectic schedules?
51. What routines kept your household running?
52. How did you teach children about money, responsibility, or faith?
53. What did you hope your children would inherit beyond possessions?
54. How did you care for relatives across generations?
55. What mistakes turned into family legends?
56. How have your relationships with children and grandchildren evolved?

Migration, travel, and change

57. Did you move away from your hometown? Why and how?
58. What did you pack first when you moved?
59. Who helped you settle into a new place?
60. How did you stay connected to people you left behind?
61. What travel memories stand out as joyful or challenging?
62. How did major historical events (wars, civil rights movements, economic shifts) affect you?
63. What technologies changed your life the most?
64. What language transitions did you navigate?

Wisdom and legacy

65. What do you wish you had known at twenty?
66. Which risks paid off in the long run?
67. What moments still make you laugh out loud?
68. How do you define success now?
69. What traditions should our family continue or reinvent?
70. How do you hope we handle disagreements after you are gone?
71. What should we teach younger generations about resilience?
72. What songs, recipes, or sayings feel like “home” to you?
73. What story do you want told at future reunions?
74. Is there anything you still want to ask us or tell us?

After the conversation

• Record a short reflection summarising what you learned and what follow-ups you owe them.
• Add names, places, and dates to your Keepsake archive so future generations can explore the context.
• Pair stories with photos, recipes, or documents you discussed.
• Schedule another session focused on a specific theme—migration, music, activism—if time ran out.

With patience and curiosity, these prompts turn time with your grandparents into a living archive future generations will treasure.

For technical peace of mind, keep the recording voice notes guide nearby so you can troubleshoot audio on the fly and capture every laugh.