Questions to Ask Your Grandparents

If there’s one thing I’ve learned over the years (besides how to pack a lunchbox in under three minutes), it’s that family stories are pure gold. And grandparents? Oh, they’re the best story tellers.

I know life gets busy but making time to sit down with Grandma or Grandpa is something you will never, ever regret. It’s like gathering little pieces of your family’s puzzle you didn’t even know were missing.

So here are some questions to ask your grandparents, because trust me, they have stories that will make you laugh, cry, and wonder how you’re even related to someone so cool.

Why You Should Ask Your Grandparents Questions (And How to Turn It Into a Game!)

First, a little pep talk. As much as we think our grandparents will always be around, the truth is, time is precious. Kids grow fast, parents get busier, and our beloved grandparents… well, they have so much wisdom, but it won’t always be there for the asking.

Let’s be real, sometimes when we think about our grandparents, it’s easy to picture them exactly as they are now: sweet, wise, maybe a little slower moving, always ready with a cookie or a lecture about how “things were different back in my day.”

But here’s the thing: our grandparents were young once, too. They ran barefoot through summers, snuck out to parties, fell in love, made mistakes, chased dreams, and lived full, exciting lives long before we ever showed up asking for another slice of cake.

Asking them questions brings all those forgotten pieces back into the light. It’s not just about gathering facts; it’s about seeing them as real, vibrant people, not just Grandma who knits or Grandpa who falls asleep in front of the TV.

You start to realize that they’ve been there, through the same nerves, excitement, heartbreak, silliness, and joy that we all go through. It builds compassion, connection, and honestly, some of the best family stories you’ll ever hear.

And why not make it a game?

Here’s a super simple and hilarious idea:

How to Play “Guess Grandpa’s Answers”

Step 1:
Have your grandparents secretly answer 10 fun questions.
(You can pick from the list below make your own!)
Make sure they write their answers down or have someone jot them for them, no peeking!

Step 2:
Once all the answers are in, gather the rest of the family together.

Step 3:
Read each question out loud and have everyone guess what they think Grandma or Grandpa said. You can even let people explain their guesses for bonus laughs.

Step 4:
After everyone guesses, reveal the real answer, and let the grandparent tell the full story behind it if they want to.

Step 5:
Keep score if you want, or just enjoy the giggles and memories as the real prize.

Why It’s So Special:

It gets everyone involved, from little kids to teenagers to adults.
It opens the door for funny, heartfelt conversations you wouldn’t normally have.
It helps kids and grandkids see their grandparents as people who were once young and wild, not just the sweet, cozy version they know today.
It creates moments that you’ll all be talking about for years to come. (“Remember when we found out Grandma used to win dance contests?!”)

And honestly, seeing your child’s eyes widen in amazement when they hear their grandpa once rode a motorcycle or their grandma once dreamed of being a movie star?

The Best Questions to Ask Your Grandparents

I put together a big list so you can pick and choose depending on your mood, their mood, and whether you’re sitting down for a long chat over tea or grabbing a quick conversation in the car.

(Also, heads up: once you get them talking, you might not be able to stop them, and that’s a good thing!)

Childhood and Family Life

These questions will open a window to a world that sounds like a different planet compared to today’s TikTok dances and iPads.

What was your house like when you were growing up?
How did you spend your summers as a kid?
Did you have any pets?
What were your parents (my great-grandparents!) like?
What’s one of your funniest childhood memories?
What games did you like to play when you were little?
Did you get an allowance? How much was it?
What was your favorite toy or thing to play with?
What did you want to be when you grew up?

Tip:
Kids love hearing about how Grandma used to build forts out of sticks or ride bikes without helmets. (Because “helmets weren’t really a thing back then”, apparently.) It makes history come alive!

School Days

School has changed a lot, but it’s fun to find the ways it’s stayed the same too.

What was your favorite subject in school?
Were you ever in trouble with a teacher?
What did you eat for lunch at school?
Did you have a best friend? What did you do together?
How did you get to school every day?
Was there a teacher who made a big impact on you?
Did you go to college or start working right after school?

Tip: Ask if they ever had to walk uphill both ways in the snow. It’s practically a grandparent rite of passage to claim this!

Love and Dating

Okay, this is where the giggles usually start.

How did you meet Grandma/Grandpa?
What was your first date like?
How did people date back then? (No apps!)
Was it love at first sight, or did it take time?
What was your wedding like?
What advice would you give about marriage and relationships?

Bonus: You might hear some very sweet (and surprisingly sassy) love stories.

Work and Career

Get ready to be amazed by how hard they worked!

What was your first job?
How much did you get paid?
Did you like your job?
What’s a funny story from your time at work?
What was the biggest lesson you learned from working?

Life Lessons and Advice

This is where the gold nuggets of wisdom start falling out.

What’s the best advice you ever received?
What’s something you wish you knew when you were younger?
How do you stay positive during hard times?
What are you most proud of?
What do you think is the secret to a happy life?

Heart Note: Write these answers down or even frame them. They might become a new family motto.

Family Traditions and Holidays

There’s nothing cozier than hearing about how the holidays used to be.

How did your family celebrate holidays?
What were your favorite family traditions growing up?
Did you cook any special foods for the holidays?
What gifts do you remember getting as a kid?
What family traditions would you like us to keep going?

Memory Maker Idea: Recreate one of their favorite traditions this year, you’ll score major brownie points with the whole family.

Fun and Random

Sometimes the best conversations come from the silliest questions.

What’s the craziest thing you ever did as a kid?
Did you ever get into trouble? (And did you get caught?)
If you could live in any time period, when would it be?
What’s something people might be surprised to know about you?
What’s your favorite joke or funny story?

Tips for Having Great Conversations

Just like with toddlers who suddenly “forget” they’re hungry at dinnertime, sometimes grandparents need a little gentle coaxing to open up.
Here are some tips:

Be patient.
They might take a while to warm up, or they might take a while to finish one story. (Embrace it!)
Use old photos.
Pull out a photo album and ask about the people and places you see.
Record the conversation.
With their permission, record your talks. These are the moments you’ll want to keep forever.
Follow up on their answers.
If they mention something surprising (“I once met a movie star!”), dig deeper.
Respect their boundaries.
If there’s something they don’t want to talk about, that’s okay too.

Make It a Family Project

Turn these chats into a fun project for the whole family:

Create a scrapbook with their stories and photos.
Write a family storybook with the grandkids’ help.
Make a “Grandparent Interview Day” every year where everyone takes turns asking questions.

Not only will you create beautiful memories, but you’ll also be teaching the next generation how important it is to honor where we come from.

I’ll be honest: Sometimes when I sit down with my kids and their grandparents, I expect a few sweet stories and some “back in my day” grumbling. But what we end up with is so much more. We laugh. We cry. We find new pieces of ourselves tucked away in their memories.

And every single time, I walk away feeling just a little more grounded, a little more grateful, and a whole lot more connected. So grab a cozy blanket, a notebook, a cup of coffee (or hot cocoa for the kids), and start asking. Your grandparents are holding onto a world of stories, just waiting for you to find them.

Questions to Ask Your Grandparents