25 best questions to ask your grandparents

Grandparents are often the keepers of a family's most valuable stories.

They've lived through different times, witnessed major historical events, built careers and families, overcome challenges, and learned lessons that can take a lifetime to acquire. Yet many of these memories are never recorded and can be lost if they're not shared.

Whether you're researching your family history, creating a life story book, or simply looking to spend meaningful time together, asking thoughtful questions is one of the best ways to preserve family memories.

At My Stories Matter, we've helped thousands of people capture their life stories and discovered that the best questions are often simple, open-ended, and easy to answer.

Here are 25 questions to help your grandparents share their stories, experiences, and wisdom.

A quick tip before you begin

The best conversations rarely follow a script. Use these questions as a starting point, but don't be afraid to ask follow-up questions when an interesting story emerges. Often the most memorable stories come from unexpected directions.

Childhood and upbringing

1. What was your favorite memory of being a child?

2. What games did you play with your friends?

3. Did you have any nicknames growing up? How did you get them?

4. What was your school experience like? Tell me about your favorite teacher.

5. What was a big challenge you faced during your childhood?

6. What traditions did your family celebrate?

7. What values were instilled in you by your parents or grandparents?

8. Did you dream about a specific career when you were young? What happened to that dream?

9. What was your first job like? What lessons did you learn from it?

10. What was a significant technological advancement you witnessed growing up?

Love and relationships

11. Tell me about the story of how you met your spouse.

12. What were some of the most romantic gestures you made for each other?

13. What qualities did you cherish most in your partner?

14. What was a big challenge you faced as a couple?

15. What advice would you give to someone starting a new relationship?

16. How did your family life change with the arrival of children?

17. Tell me about your proudest moments as parents.

18. What are some of the most valuable lessons you learned from your parents?

19. What does family mean to you?

20. What makes a long-lasting and fulfilling relationship?

Life lessons and world events

21. What major historical events do you remember vividly?

22. How did these events impact your life and your community?

23. What should young people know about these events?

24. What concerns do you have for the future?

25. What change are you most happy to have seen during your lifetime?

Bonus question

Is there anything you wish you could tell your younger self?

These questions are simply a starting point. The most meaningful conversations often happen when one answer leads naturally to another memory, story, or life lesson.

Take your time, listen carefully, and encourage your grandparents to elaborate. You may be surprised by the stories you've never heard before.

What to do with their answers

Asking questions is only the first step. The real value comes from preserving the stories that emerge.

You might record the conversation, write down key memories, collect old photographs, or create a life story book that future generations can enjoy.

Many families are surprised by how quickly a simple conversation uncovers stories that might otherwise have been lost forever.

At My Stories Matter, we help families preserve interviews, memories, photographs, and life lessons in beautifully designed life story books. Whether you're recording a grandparent's childhood memories or documenting a lifetime of experiences, the goal is the same: ensuring these stories can be shared, enjoyed, and treasured for generations to come.