50 questions to ask your grandfather, at his own pace

Keeping a few good questions to ask your grandfather in your pocket can turn an ordinary visit into one of your family’s most valuable records. Your grandfather may enjoy being invited to tell stories — and with the right question, out come stories about the places and times he lived through, about courage, love and the choices that explain who you are today.

Here are 50 questions, organized by the stages of his life. They are not meant to be asked all at once: pick a handful per visit, let the conversation flow and save the rest for next time.

His roots and childhood

1. What was the house where you grew up like? Did it have electricity, running water?
2. What game did you love most as a boy?
3. What was the most mischievous thing you ever did?
4. What were your parents like? What did you inherit from each of them?
5. Did you have a nickname? Who came up with it?
6. What was school like in your day? Did you like studying?
7. What smell takes you straight back to childhood?
8. What did your family eat on Sundays?
9. Who was your best friend growing up? What happened to him?
10. What is your very earliest memory?

Youth and friendships

11. What were you like at twenty? What were you afraid of, and what gave you courage?
12. What music played at the parties of your youth?
13. Do you remember your first love? What was dating like back then?
14. Did you leave your parents’ home early? How did that go?
15. What did you and your friends do for fun?
16. Did you ever get into trouble you only just escaped?
17. What dream did you have back then — and what became of it?
18. Was there an older person — a teacher, a boss, a neighbour — who changed your direction?

Work, courage and a changing world

19. What was your first job, and how much did you earn?
20. What did you do with your first pay?
21. Did you have to leave your town to work? What was it like to start over?
22. Which invention changed your life most — TV, the car, the telephone?
23. What was the hardest day of your working life?
24. And the day you are proudest of?
25. What was it like to support a family back then?
26. Did you ever go through a financial squeeze? How did you get through it?
27. Which trade or skill of yours does almost nobody know about?
28. If you could go back, would you choose the same line of work?

The places and events he lived through

29. Which cultural or sporting event did you want to follow? Where were you?
30. Which change in technology do you remember living through, in Canada or elsewhere?
31. Was there news that changed daily life in your community? Would you like to talk about it?
32. Which object did you keep from an important time, and what does it represent?
33. What were the gatherings and streets like where you lived?
34. Which place changed a lot during your life — or stayed much the same?
35. Which change did you appreciate in the places you lived, and what do you miss?

Love and family

36. Which important relationship in your life would you like to talk about? How did it begin?
37. If there was a marriage or another commitment you want to remember, how did you decide to celebrate it?
38. If fatherhood is part of your story, how did you experience that arrival, through birth, adoption or another bond?
39. How did the relationship begin in which people started calling you Grandpa? What does it mean to you?
40. Which story of our family must not be lost?
41. Which relative from long ago do you miss most? What were they like?
42. Which tradition in your home did you insist on keeping?
43. What have you learned about love over all these years?

Wisdom and advice

44. What are you proudest of in your life?
45. Which mistake taught you more than any success?
46. What would you tell the young man you were at twenty?
47. What, for you, makes a life worth living?
48. What advice do you want to leave your grandchildren and great-grandchildren?
49. How would you like to be remembered?
50. Is there a story you have never told anyone — and would you be willing to tell it now?

For an even fuller base, see our guide on what to ask your grandparents, organized by stage of life. To involve the children, we also have questions from grandchildren to grandparents.

How to record the answers

Asking the questions is only half the job. The other half is keeping the answers before they are lost. If he agrees, record audio: your grandfather’s voice, accent and pauses are worth as much as his words.

Later, these recordings can become a grandparents’ memory book — your grandfather’s story, told by him and kept for the next generations.

Ask about the events he chooses to remember

Your grandfather may have lived through a neighbourhood changing in Toronto, worked in another province or spent part of his life outside Canada. Ask which public events he actually followed and what changed in his daily life. Do not pick a sports victory or a national crisis as the required memory of his generation. An ordinary story about neighbours or getting around may say more about his life than a list of major events.

Further reading: Oral History Association — participants.