The Questions I Wish I’d Asked My Grandpa
When I was younger, I thought my grandpa would always be there.
He sat in the same chair. Told the same jokes. Ate the same snacks. He had a way of making the world feel stable, like nothing really changes if you don’t look too closely.
And because I believed he was permanent, I asked him permanent questions.
“How was your day?”
“Did you watch the game?”
“How’s the weather?”
Good questions. Small questions. Safe questions.
But now that he’s gone, I find myself wishing I asked different ones.
Not because I needed a perfect interview. I just needed more of him.
If you’ve ever wondered, “What questions should I ask my grandparents about their life?” here’s what I’ve learned: the best questions aren’t the clever ones. They’re the ones that make someone feel seen.
The Real Goal: Not Facts, But Meaning
A lot of people think interviewing a grandparent is like collecting data.
Where were you born?
What year did you graduate?
Where did you work?
Those matter, but that’s not what your kids and grandkids will treasure most.
They will treasure the stories behind the facts.
What did it feel like to leave home?
Who believed in you when you doubted yourself?
What did you learn the hard way?
What are you proud of?
What do you wish you did differently?
That is the difference between family history and family legacy.
25 Questions to Ask Your Grandparents
Here are questions you can use if you’re recording an oral history or just having a meaningful conversation on a normal Tuesday.
Childhood and Home
What did your house look like growing up?
What was a normal day like when you were 10?
Who did you feel safest with as a kid?
What did your parents do that you now understand as an adult?
What’s a smell or sound that instantly takes you back?
Love and Relationships
How did you meet your spouse, or your first love?
What did you learn about marriage from the people around you?
What’s something you wish you would have said sooner?
Who was a friend that shaped you?
What do you think makes a good life?
Work, Calling, and Hard Seasons
What was your first job and what did it teach you?
What was the hardest season of your life?
Was there a time you almost gave up?
Who helped you through it?
What are you proud you endured?
Family and Values
What values do you hope our family never loses?
What did you want to be remembered for when you were younger?
What do you want to be remembered for now?
What did you learn from your own grandparents?
What do you think younger generations misunderstand?
Stories You Want Preserved
What’s a story you hope gets told at your funeral?
What’s the funniest thing that ever happened to you?
What’s a moment you still replay in your mind?
What’s a decision that changed your life?
If you could send a message to your great-grandkids, what would it be?
How to Get Them to Open Up
If you’re thinking, “My dad won’t talk about his past,” you’re not alone.
A tip that works more often than you’d expect: start with details, not emotions.
Instead of “Tell me about your childhood,” try:
“What was your neighborhood like?”
“What did your mom cook when she wanted to make everyone happy?”
“Who was the best storyteller in your family?”
Details build comfort. Comfort builds depth.
From Conversation to Heirloom
You can absolutely record these stories on your phone. And you should.
But if your goal is to create something your family will watch for generations, a video memoir turns those stories into a true family heirloom. It becomes a personal documentary, a living legacy video, and a way to preserve family history with clarity and care.
If you want help interviewing a parent or grandparent, Roots & Story offers a video memoir service designed to make this easy and meaningful for your whole family.
