Questions to Ask Grandpa: 75+ Conversation Starters

Your grandpa has lived through wars, recessions, and decades of change. He's worked jobs that no longer exist. He's loved, lost, and learned lessons you'll never find in books. But unless someone asks him about it, those stories stay locked away.

The right questions unlock those stories. They help grandpa share his world with you. They create moments your family will treasure for years.

I've put together 75+ questions that work. They're sorted by topic so you can pick what fits your grandpa best. Some are light and fun. Some go deep. All of them will get him talking.

Article Snapshot

Childhood questions reveal the world your grandpa grew up in
Career questions uncover lessons about work, grit, and finding purpose
Love story questions preserve romantic history your family will treasure
Life wisdom questions capture advice worth passing to future kids
Historical questions connect your grandpa's life to world events
Recording these talks preserves his voice and stories forever

How to Get Grandpa Talking

Before you start asking questions, set the stage. Pick a quiet time when grandpa isn't tired or rushed. Sit somewhere comfy. Let him know you want to hear his stories—and mean it.

Some grandpas talk freely. Others need time to warm up. Start with easy questions about childhood or hobbies. Save the deep stuff for later when he's in the flow.

Here's a tip: bring old photos if you have them. Photos spark memories better than any question. Let grandpa hold them, look at them, and tell you what he sees.

Questions About Grandpa's Childhood

Every grandpa was once a kid. He played games, got in trouble, and dreamed about the future. These questions take him back to those early years when life was simpler but full of wonder.

What is your fondest childhood memory, and why does it stand out?
Describe the home where you were born or grew up.
Where was your hometown, and what comes to mind when you think about it?
What was a typical day like for you as a kid?
What games or activities did you love as a child?
What things did you get in trouble for as a kid?
What's your earliest memory?
Who was your childhood hero?
Who was your best friend growing up? What were they like?
What were your favorite meals or foods as a child?
What were your favorite movies or shows as a kid?
What childhood lesson has stayed with you into adulthood?
Did you have a curfew growing up? Did you ever break it?
What did you get in trouble for that your parents never found out about?

These questions often lead to the best stories. Grandpas light up when they talk about their youth. You might hear about pranks, first crushes, or adventures you never knew happened.

If you want more childhood questions, check out our guide to fun questions to ask older adults.

Questions About Grandpa's Career

Work shaped a huge part of grandpa's life. He spent decades earning a living, facing challenges, and building skills. These questions help him share that journey.

How did you choose your career, and what did you enjoy about it?
What was your first job? What lessons did it teach you? How much did you make?
What made you successful at work?
What 1-3 work achievements are you most proud of?
How has your industry changed since you started?
What advice would you give someone starting out in your field?
Did you ever make a big career change? What prompted it?
How did you balance work and family?
What was a turning point in your career?
What would you do differently if you could?

The "first job" question works great. Grandpas love telling you what they earned and what things cost back then. Let them have that moment—it's part of the fun.

Questions About Love and Marriage

Behind every grandpa is often a love story. How he met grandma. The early years. The ups and downs. These stories add depth to your family history that facts alone can't capture.

These questions work whether grandma is still here, has passed, or if grandpa had more than one great love. The focus is on memories, not current status.

How did you meet your spouse, and what first attracted you to them?
Can you share a story from early in your relationship?
What has been the key to a strong marriage?
What advice would you give to newlyweds?
What challenges did you face together, and how did you get through them?
What traditions did you create together that were special?
How did you handle arguments or conflicts?
When you think about your spouse, how would you describe them?
What's something your spouse did that surprised or touched you deeply?
How did your views on love change over the years?

These questions often produce the sweetest stories. Be patient. Grandpa might need a moment to gather his thoughts—or his emotions. That's okay.

Questions About Family History

Grandpa is a living link to your family's past. He knows names, places, and stories that will disappear when he's gone. These questions help capture that history while you still can.

Can you trace our family tree back as far as you remember?
Where did our family originally come from?
Do you know the story behind our family name?
Are there any famous or notable people in our family history?
What were common jobs or trades in our family?
Do we have any heirlooms? What are their stories?
What languages were spoken in our family?
Were any ancestors part of major historical events?
What traditions got passed down through our family?

Bring a notebook for this section. You'll want to write down names and dates. Better yet, record the talk so you can go back and fill in details later.

For a deeper dive into family history, our questions to ask your grandparents guide covers even more ground.

Questions About Life Lessons and Wisdom

Grandpa has decades of wisdom stored up. But he might not share it unless you ask. These questions invite him to pass down what he's learned—the stuff that matters most.

What values do you hope to pass on to future kids?
What is a lesson you've learned that you want to pass on?
What's your biggest piece of advice for young people today?
How do you want to be remembered?
What do you believe is crucial for younger people to understand?
What achievements are you most proud of?
What mistakes taught you the most?
How has your view of legacy changed as you've aged?
What traditions do you hope continue after you're gone?

These questions can get emotional. That's okay. The answers are often the most valuable things grandpa can give you. They're his legacy in words.

Questions About Historical Events

Your grandpa lived through history. He saw events you've only read about. These questions connect his personal story to the bigger picture of the world.

What historical events had the most impact on you?
What's the first major news story you remember from childhood?
What big historical event do you remember happening?
What technology change affected you the most?
Are there any historical figures you admire? Why?
What part of history fascinates you the most?

Grandpas often have vivid memories of where they were during major events. Where they were when news broke. How their town reacted. These personal details bring history to life in ways textbooks never can.

Fun and Lighthearted Questions

Not every question needs to be deep. These lighter questions bring out grandpa's playful side and often lead to the funniest stories.

What's the worst haircut you've ever had?
What fashion trend do you regret following?
What's a joke or prank that still makes you smile?
What's the weirdest thing you believed as a kid?
Do you remember laughing so hard you cried? What caused it?
What silly tradition did you share with friends or family?
What comedian always makes you laugh?
What is one of the greatest pranks you've pulled?

Save a few of these for the end of your talk. They leave things on a happy note and remind grandpa that sharing stories can be fun.

Questions About Family Traditions

Traditions tie families together across time. Grandpa knows where yours came from and why they matter. These questions help preserve that knowledge.

What family traditions do you hold most dear? How did they start?
What role does food play in our family traditions?
What holiday tradition do you remember most from childhood?
Are there traditions you started with your own family?
How have our family traditions changed over time?
What traditions do you hope continue?

Tradition questions often lead to recipe sharing, old photos, and stories about relatives who are no longer here. Be ready to go wherever the talk takes you.

How to Preserve These Stories

Asking questions is only the first step. The real value comes from preserving what grandpa shares so future family can hear it too.

Record audio or video. A phone recording captures grandpa's voice. Video captures his expressions, his gestures, his way of telling a story. Both are priceless.

Take notes. Write down names, dates, and places. You'll forget details if you don't capture them in the moment.

Go back for more. One talk won't cover everything. Plan to revisit topics. Grandpa will remember more once he starts thinking about the past.

Share with family. Send recordings to siblings, cousins, and aunts. These stories belong to everyone.

If you want help doing this right, Telloom offers guided video interviews with studio-quality gear. We've helped hundreds of families capture their grandparents' stories in a format that lasts forever.

Start With One Question

You don't need hours of time. You don't need a special occasion. Just pick one question from this list and ask it the next time you see grandpa.

Maybe it's over breakfast. Maybe it's on a walk. Maybe it's during a holiday visit. The setting doesn't matter. What matters is that you ask—and that you listen.

Grandpa's stories are worth hearing. His wisdom is worth keeping. And once he's gone, you'll be glad you took the time to capture them.

Ready to preserve your grandpa's stories in studio-quality video? Schedule a free planning call with Telloom to see how we can help your family capture his voice, his humor, and his wisdom for kids not yet born.