
10 Questions That'll Get Your Grandparents Talking (And You'll Be Glad You Asked)
The best family stories aren't lost to time. They're just waiting for the right question.
We all know we should ask our grandparents about their lives. But where do you start when you're sitting across from someone who's lived through eight decades of history, heartbreak, and probably more than a few questionable fashion choices?
Here are 10 questions that actually work. The kind that turn a quick cuppa into an afternoon you'll both remember.
10 Questions to Ask your Grandparents
1. "What could you smell when you walked through your childhood front door?"
Forget asking about the layout of their house. Smells unlock memories like nothing else. Was it Nan's lamb roast? Cigarette smoke and Brylcreem? The damp from the laundry that never quite dried?
This question takes them straight back. You'll get far more than a floor plan.
Try asking:
- "What sounds did you wake up to?"
- "Where did everyone sit at dinner?"
- "What was different about houses back then?"
2. "How did you two actually meet?"
You might think you know this one, but you probably only have the sanitised version. Push for details:
- What were they wearing?
- What did they say to each other?
- Were their parents horrified?
- How long before they knew?
Love stories are never boring when you get the full version.
3. "What's the happiest you've ever been? The kind of happy you can still feel?"
This question cuts through the "expected" answers (weddings, births, promotions) to something more honest. Sometimes it's a Tuesday afternoon in 1974 when nothing special happened at all.
4. "What was the hardest thing you ever had to do?"
This one takes courage to ask. And to answer. But stories of resilience matter. You'll learn:
- How they found strength they didn't know they had
- Who showed up for them
- What actually helped (and what didn't)
- How it changed the way they saw the world
5. "Why did we always do [that weird family thing]?"
Every family has them. The traditions that make perfect sense to you but would baffle anyone else. Christmas prawns instead of ham. Pancakes on Sunday nights. The way Grandad always knocked three times.
Understanding the why is how traditions stay alive instead of just feeling like obligation.
6. "What do you remember about your grandparents?"
This one extends your family tree back four generations in a single conversation. Ask about:
- What they were like as people (not just "nice" or "strict")
- Jobs they had, places they lived
- Stories they told
- How the world was different then
7. "What's something that was completely normal when you were young that would shock people today?"
This is where it gets interesting. Maybe it's that kids rode in car boots, or that women couldn't have their own bank accounts, or that you could smoke on planes.
These stories aren't just nostalgia. They're social history told through someone who was actually there.
8. "What are you most proud of that nobody really knows about?"
This question gives them permission to brag a bit. And they should. Everyone's done something quietly brilliant that never makes it into casual conversation.
9. "What would you tell yourself at 25?"
Wisdom that's actually useful tends to be specific:
- Not "work hard" but "take that job in Adelaide even though it scares you"
- Not "family matters" but "ring your sister more. You'll regret it later"
10. "What do you want us to remember about you?"
Give them the space to say what matters. This isn't morbid. It's generous. You're letting them shape their own story.
How to Actually Have These Conversations
Don't make it an interview. Just ask one question over a coffee or while you're doing the dishes together. If they're on a roll, let them talk. If they need time, that's fine too.
Bring photos if you can. Old pictures are memory gold. "Who's that bloke in the background?" often leads to the best stories.
Record it (but be chill about it). Just say, "Mind if I record this? I don't want to forget the details." Most people are fine with it once they start talking.
Ask follow-ups. "Tell me more about that" is the best question you'll ever ask.
Share your own stuff too. Make it a conversation, not an interrogation. When they mention their first car, tell them about yours.
The Bit Where We're Honest
Look, we know the clock's ticking. But here's the thing: one conversation is infinitely better than none. And it doesn't have to happen all at once.
Start with whichever question feels easiest. See what happens. These aren't the only questions worth asking. They're just the ones that tend to open doors.
And yes, we built Keepsake specifically to help with this. Because we reckon the best stories are the ones you create with people, not just about them. But even if you never use our platform, please just ask the question.
Your grandparents have lived entire lives you know almost nothing about. Their stories are funny, strange, heartbreaking, and completely unique. And they're usually just waiting for someone to ask.
So ask.