100 Questions to Ask Your Grandparents, Grouped by Life Chapter

Someday you'll want to hear it in their own voice: how they met, what their first job paid, what their parents were like. These questions make it easy to start. Pick a chapter, ask a few at a time, and let the conversation wander. The detours are often the best part.

Tip: Record the answers on video. A written note keeps the facts. A video keeps their laugh, their pauses and the way they tell it.

Childhood (1–15)

  1. Where were you born, and what was the house like?
  2. What's your earliest memory?
  3. What were your parents like when you were small?
  4. Did you have brothers or sisters? What were they like as kids?
  5. What did your family eat for dinner on a normal night?
  6. What was your favorite toy or game?
  7. Who was your best friend growing up?
  8. What chores did you have?
  9. What did you get in trouble for?
  10. What was your neighborhood like?
  11. How did your family celebrate holidays?
  12. What did you want to be when you grew up?
  13. Was there a song, show or radio program you loved?
  14. What was the best gift you got as a child?
  15. What's a smell or sound that takes you right back?

School years (16–25)

  1. What was your school like?
  2. Who was your favorite teacher, and why?
  3. What subject did you love, and which did you dread?
  4. How did you get to school?
  5. What did kids do for fun after school?
  6. Were you ever in a club, team or band?
  7. What did you wear back then that would surprise us?
  8. Did you have a first crush?
  9. What was the biggest news story you remember from those years?
  10. What did you do the day you finished school?

Young adulthood (26–37)

  1. What was your first job, and what did it pay?
  2. When did you first leave home?
  3. What was your first car, or how did you get around?
  4. What did you do on a Saturday night?
  5. Who were your closest friends then?
  6. What was the bravest thing you did in your twenties?
  7. Did you ever travel somewhere that changed you?
  8. What did you think your life would look like?
  9. Did you serve in the military? What do you want us to remember about it?
  10. What was the hardest lesson you learned early?
  11. What did things cost back then that surprises people now?
  12. What's a decision from those years you're proud of?

Love and marriage (38–49)

  1. How did you meet Grandma / Grandpa?
  2. What was your first impression?
  3. What was your first date?
  4. How did the proposal happen?
  5. What was your wedding day like?
  6. Where did you live first as a couple?
  7. What did you argue about early on, and how did you work it out?
  8. What's a favorite memory of the two of you?
  9. What do you think makes love last?
  10. What did your parents think of your partner?
  11. Is there a song that's "yours"?
  12. What would you tell a young couple today?

Raising a family (50–62)

  1. What do you remember about the day my parent was born?
  2. How did you pick their name?
  3. What were they like as a child?
  4. What was a typical day when your kids were little?
  5. What family traditions did you start?
  6. What was money like in those years?
  7. What was the funniest thing one of your kids ever did?
  8. What was hardest about being a parent?
  9. Did you ever move with the family? Why?
  10. What vacations or trips do you remember most?
  11. What did you hope for your kids?
  12. What do you wish you'd done differently?
  13. What made you proudest?

Work and purpose (63–71)

  1. What jobs have you had over your life?
  2. Which one did you like most?
  3. Who was the best boss or mentor you had?
  4. What was a typical workday?
  5. What skill are you proudest of?
  6. Was there a time you took a big risk at work?
  7. What did you do when things got hard?
  8. What did work teach you about people?
  9. If you could have done any job, what would it be?

Family roots (72–81)

  1. What do you know about your grandparents?
  2. Where did our family come from?
  3. Are there family stories that get told again and again?
  4. Is there a family recipe? Will you walk us through it?
  5. Are there heirlooms, and what's the story behind each?
  6. Were there any family characters everyone talked about?
  7. What languages were spoken in your home?
  8. What did your family believe in or care about most?
  9. Is there a photo you'd like to tell the story behind?
  10. What do you want the great-grandkids to know about where they come from?

Big moments and changing times (82–90)

  1. What historic event do you remember most clearly? Where were you?
  2. What invention changed your life the most?
  3. What's the biggest way the world has changed since you were young?
  4. What's something that's better now? Worse?
  5. What was the hardest time you lived through, and how did you get through it?
  6. Who helped you most when you needed it?
  7. What's a moment you laughed until you cried?
  8. What's a day you'd love to live again?
  9. Is there a story you've never told us?

Wisdom and wishes (91–100)

  1. What are you most grateful for?
  2. What matters most to you now?
  3. What do you know now that you wish you'd known at 20?
  4. What's the best advice you ever got?
  5. What advice would you give each of your grandkids?
  6. What do you want to be remembered for?
  7. What still makes you happy every day?
  8. Is there anything you'd still like to do?
  9. What do you love most about our family?
  10. What would you like to say to future generations watching this?

How to use these questions

Save their answers with Talesake

Talesake is a family video story app. Family members send questions, and Grandma or Grandpa answer on video, from a phone, whenever they're ready. The stories stay together in one private family library, protected with standard encryption, and you can export them anytime.

Setup and the first chapter are free. After that, plans are $99/yr (Regular) or $149/yr (Premium).

Start your family's first chapter free →