25 Best Questions to Ask Your Grandparents



Grandparents are the custodians of our family history, holding a wealth of stories and experiences that enrich our lives. Yet, these stories can fade away as time passes if not shared and preserved. Engaging with grandparents through meaningful conversations not only strengthens family bonds but also provides invaluable insights into your heritage. Whether you're compiling a family tree, creating a legacy project, or simply seeking to deepen your connection, these questions to ask your grandparents will unlock a treasure trove of memories! 

At My Stories Matter, we’ve researched what makes for good questions that are both easy to answer and provide meaningful responses.

Here are the 25 best questions to ask your grandparents, ensuring their stories continue and resonate with your children and grandchildren.  

Questions to Ask Grandparents: 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?

Questions to Ask Grandparents: Love and Relationships 

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

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

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

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

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

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

  7. Tell me about your proudest moments as parents.

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

  9. What does family mean to you?

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

Questions to Ask Grandparents: World Events

  1. What major historical events do you remember vividly?

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

  3. What should young people know about these events?

  4. What concerns do you have for the future?

  5. What change are you happy to have seen in your lifetime?

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

These are just starting points. Let the conversation flow organically, allowing your grandparents to share their unique stories and perspectives. Encourage them to elaborate and reminisce, painting a vivid picture of their past. 

Record Their Answers on My Stories Matter 

Now, where to record their answers? My Stories Matter offers the key to unlocking this extraordinary potential, FOR FREE!

My Stories Matter empowers you to:

  • Find inspiration: Find even more prompts (with pictures!), play nostalgic songs for your grandparents, and make the journey of reminiscing fun for you and them.

  • Preserve it securely: Store their stories safely and securely in the cloud, accessible to authorized family members anytime, anywhere.

  • Collaborate as a family: Invite extended family to contribute, weaving a collective tapestry of shared memories.

  • Leave a lasting legacy: Pass down your family's history in a beautiful, engaging format that future generations will cherish.

If you want more than just a digital legacy, My Stories Matter can also create a publication-worthy book. All you have to do is share your grandparent’s stories, and we’ll handle the rest! You get to: 

  • Choose from a variety of fonts, colors, and styles to find the perfect look.

  • Restore and colorize images from the past.

  • And more!

Expert designers will ensure their memories are preserved in a publication-worthy book.

Here's what our previous clients are saying about My Stories Matter’s book quality: 

“The book arrived in excellent condition. Everything about it screams quality, from the binding, photo quality, formatting, and paper thickness. When I was turning the pages, each page felt like two because of the quality of the paper. Thank you for bringing the project to fruition.” 

There’s no downside to trying it FOR FREE! Capture a Lifetime of Memories in Minutes!


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