Things to Ask Your Grandparents: 100+ Questions

Article Snapshot

Grandparents carry irreplaceable family history, practical wisdom, and stories from eras we can only read about
Questions organized into 10 categories covering every aspect of their lives
Both light conversation starters and deeper questions about legacy
Practical tips for making these conversations happen naturally

Most people wish they'd asked more questions. After a grandparent dies, the regret is always the same: "I never asked about..." followed by something that now can never be answered.

The thing is, grandparents rarely volunteer their life stories. They assume no one is interested, or that the past isn't relevant, or that their experiences aren't special enough to share. They need to be asked.

This guide gives you 100+ specific things to ask your grandparents. Some are light and easy. Some go deeper. All of them open doors to stories that would otherwise stay locked away.

For more questions organized by specific relationships and occasions, see our complete questions to ask family members resource.

Things to Ask About Their Early Life

Childhood questions are usually the easiest place to start. They're emotionally lighter and often lead to vivid, detailed stories.

Where were you born, and what was that place like?
Describe the house where you grew up.
What was a typical day like when you were 10 years old?
What games did you play as a kid?
Who was your best friend growing up?
What did you want to be when you grew up?
What was your favorite subject in school? Your least favorite?
What did you get in trouble for?
What's your earliest memory?
What was your favorite food as a kid?
What did your neighborhood look like?
Did you have any pets?

Things to Ask About Their Parents and Ancestors

Your grandparents are the last living connection to great-grandparents and earlier generations. What they remember is the only window you have.

What were your parents like? How would you describe them?
What did your parents do for work?
How did your parents meet?
What did your parents teach you that you still remember?
What was the hardest thing your parents went through?
Where did our family originally come from?
Why did our ancestors immigrate or move?
Are there any family stories about relatives from long ago?
Do you know the origin of our family name?
What languages were spoken in your family growing up?
Is there anyone in the family tree whose story we should know?

Things to Ask About Historical Events

Your grandparents lived through events you can only read about. Their personal experience adds something no history book can capture.

What big historical event do you remember most clearly?
What was it like living through [specific event]?
What's the first major news story you remember from childhood?
How did technology change most dramatically during your life?
What invention or change affected your daily life the most?
What world events worried you when you were young?
Did anyone in the family serve in the military? What do you know about their experience?
What social changes have you witnessed over your lifetime?

Things to Ask About Work and Career

Work often defined a huge part of life for previous generations. These questions can reveal stories about ambition, struggle, and what providing for a family meant.

What was your first job? How much did you earn?
How did you choose your career?
What did you like most about your work?
What was the hardest part of your job?
Did you ever change careers? What prompted that?
What professional achievement are you most proud of?
What advice would you give someone just starting their career?
How did you balance work and family?
Is there something you wish you'd done differently career-wise?
What boss or mentor influenced you most?

Things to Ask About Love and Relationships

How your grandparents met, fell in love, and built their life together is part of your family's origin story.

How did you two meet?
What was your first impression of each other?
What was dating like back then?
How did you know this was the person you wanted to marry?
What was your wedding day like?
What made your relationship work over the years?
What was the hardest period in your marriage?
What do you wish you'd known about relationships when you were young?
What advice would you give couples today?
What still makes you laugh together?

Things to Ask About Being Parents

Your grandparents raised your mom or dad. Understanding their parenting experience connects you to your family's story.

What was it like becoming a parent for the first time?
What surprised you most about raising children?
What was the hardest part of parenting?
What values did you try hardest to teach your kids?
What's your favorite memory with my mom/dad when they were young?
Is there anything you'd do differently as a parent?
How is raising kids different today versus when you did it?
What did you learn from your kids?

Things to Ask About Family Traditions

Family traditions are the rituals that make a family feel like home. Understanding where they came from helps preserve them.

What family traditions do you remember from childhood?
How did your family celebrate holidays?
What traditions did you start with your own family?
Is there a tradition that faded away that you wish we still did?
What role did food play in your family gatherings?
Are there any recipes that have been passed down?
What traditions do you hope we'll continue?

Things to Ask About Life Lessons

Decades of living teach things that can't be learned any other way. These questions invite your grandparents to share what they've learned.

What's the most important lesson life has taught you?
What advice would you give your younger self?
What mistake taught you the most?
How have your priorities changed over the years?
What do you wish young people understood?
How do you stay positive when life is hard?
What does a good life look like to you now?
What's something you changed your mind about over time?

Things to Ask About Legacy

These deeper questions show your grandparents that their life matters to you. Many appreciate being asked directly.

How do you want to be remembered?
What are you most proud of in your life?
What values do you hope our family carries forward?
What do you want future generations to know about you?
What stories should our family never forget?
What contribution to our family or community matters most to you?
How has your idea of legacy changed as you've gotten older?

Lighter Things to Ask

Not every question needs to be deep. Sometimes the best stories come from playful questions.

What's the most mischievous thing you ever did?
What fads from your youth seem funny now?
What was your favorite movie or music when you were young?
Did you ever have a celebrity crush?
What piece of technology amazed you when it first came out?
What's the funniest thing that ever happened to you?
What hobby have you kept your whole life?
What's your favorite vacation memory?
What's a book or show you loved?

How to Have These Conversations

The questions are only part of it. How you ask matters too.

Choose the right moment. Don't pull out a list during a busy family dinner. Find quiet moments, perhaps looking at old photos or sitting together after a meal.

Start with easy questions. Childhood and lighter topics warm people up. Save the deeper legacy questions for later conversations.

Use objects as prompts. "Tell me about this photo" or "Where did this come from?" are easier to answer than abstract questions about life.

Follow their lead. When they mention a name, place, or event, ask more about it. The best stories come from follow-up questions.

Record when possible. With permission, record audio or video. Their voice, expressions, and way of telling stories are as valuable as the stories themselves.

Don't do it all at once. Multiple shorter conversations over time capture more than one marathon session.

Start Today

Family stories disappear every day. Once a grandparent is gone, their memories go with them, no matter how much we wish we'd asked more questions.

You don't need to work through this entire list. Pick two or three questions that feel right. See where the conversation leads. Come back with more questions next time.

For additional questions organized by relationship, life theme, holiday, and milestone, explore our complete questions to ask family members guide with 640+ conversation starters.

Things to Ask Your Grandparents: 100+ Questions Worth Asking