37 Great Questions to Ask Older People or Grandparents

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Elders are a treasure trove, especially when it comes to what they have learned about life. Maybe you'll discover some philosophy, strange historical data, or secret revelations. 

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You may even hear difficult stories about pain, struggles, or even death, but consider asking the questions, anyway. Whatever they say, you might want to hear — and heed — their advice.

Questions to Ask Older Adults About Their Childhood

The world changes with every generation. Plus, with increasing technological advancements, those days seem more and more unrecognizable.

1. “Did you ever have a curfew?”

This question could elicit several stories about mischief. Plus, you'll discover something called free-range parenting.

2. “How did you get to school?”

This question should give some perspective on riding the bus. Most parents didn't buy their kids cars at age 16, although kids today think they automatically deserve one.

3. “Who was your favorite teacher?”

This tells you two quick things about someone. One, you'll find out whether he or she loved English and hated science and how that impacted a future career choice. 

4. “What was the worst trick you played on your parents?”

Some shenanigans are worth retelling. This question lets you find out whether an older adult was an angel or a little naughtier than that.

5. “Did you ever face any disadvantages?”

What you may find is that the person with whom you are talking sees life as a complete journey. Maybe he or she was propelled forward by the very thing that was supposed to hold him or her back.

6. “Who was your first crush?”

There was a time when there weren't cellphones, social media, or Snapchat. In fact, there was a time when the phone line had something called a party line.

7. “Did you ever play an instrument?”

You might learn about a giant accordion on the school bus every day of the week. Or maybe there was a college scholarship to play in the college orchestra. You may even learn that an elder gave everything up to start a family.

8. “Was there ever a time when you couldn’t afford to eat?”

Even if an elder never faced food insecurity, he or she knew someone who did. This opens the door for an essential history lesson on how people used to treat the impoverished "back when."

Questions to Ask Older People About Adulthood

Can you imagine raising a family of six on $25,000 per year? If you think life is a struggle now, just wait until you hear how it could have been.

9. “What’s the difference between knowledge and wisdom and why does it matter?”

There's a point in time when people start to realize what does and what doesn't matter. Maybe an elder can help you get there sooner, rather than later.

10. “How many hours a week did you work, and did you have a pension?”

Skip money specifics. Instead, try to find something out about labor unions, employment expectations, or how an elder raised four kids on little money.

11. “What five things have you discovered that are most important in life?”

Whatever the response, maybe it will help you to understand which things to validate, and which to ignore.

12. “What was your first apartment like?”

More and more young adults find it impossible to rent apartments on their own, so they stay at home longer. Living on $150 a month was more common than you think.

13. “What was your first car?”

This question is about more than the car itself. It's also about the struggle it took to earn enough to pay for a vehicle.

14. “How many jobs did your dad have before he found his career?”

The older generations generally had one job and one career throughout their whole lives. That said, you may find out something interesting about how young they started to work and what that early labor taught them.

15. “Were you ever fired from a job?”

You may find out that an elder stood up for what was right and was fired for it. If so, it’s a good lesson in courage you'll never forget.

16. “How did you buy your first home?”

Inflation is crazy now, but the Great Depression had lasting impacts on families’ financial situations. Oftentimes, families only had one breadwinner.

Questions to Ask Grandparents to Learn About Your Family

Be prepared to learn some amazing details about your family filled with love, loss, hope, and tragedy.

17. “What was your first memory of me?”

This question can lead to some answers about your family history. Or you might find out about things like rural healthcare, a change in hospital norms, or a lack of car seats.

18. “How did the war affect the family?”

Serving one's country impacted generations in ways that you may not even be aware of. Maybe you learn that your ancestors escaped to Canada during the Civil War or somewhere else in the world.

19. “Did anyone ever have polio?”

After kids returned from living in iron lungs, their stories made small-town newspaper headlines. Adults who contracted polio could uproot and devastate families.

20. “Did our family ever survive a devastating disaster or financial blow?”

Learning about how your grandparents managed to outmaneuver tragedy and turn their financial life into a success story is a great lesson to learn.

21. “Who was the first person to go to college?”

By 8th grade, kids were once learning as much as today's high school seniors. College was something that was either unnecessary or unaffordable for some people.

22. “Did you have any siblings that didn’t make it?”

Some family trees were bigger long ago. You may discover that yours could have been a lot bigger.

23. “How did you meet grandma or grandpa?”

Everyone loves to hear this story. Make them repeat it.

Funny Questions to Ask Older Adults

Most older adults have an unusual or innocent style of humor. Get them going, and you'll all be gut-laughing in no time.

24. “What’s the one thing your dad or grandpa told you, but you ignored, that came back to bite you?”

Older adults often gained wisdom through a lot of trial and error and all without a safety net — or padding. The way they got back up and dusted themselves off is more what the story is about than anything.

25. “What was the worst thing you got in trouble for?”

You might find this answer to seem a bit boring by today's standards. Or you might be surprised to hear that they made it out of childhood in one piece.

26. “What tricks did you used to play on your siblings?”

Maybe you can swap stories on this one and see who was more savvy or successful as a  juvenile delinquent.

27. “What was your first run-in with the law?”

This question brings out the comedy when you find out what happened when Grandpa told his parents about the teenage drinking binge or the speeding ticket.

28. “How did you turn the mundane bits of life into an adventure?”

When someone unleashes creativity in the face of boredom, you may find some astonishing results worthy of vows to not repeat what was said.

29. “What’s the most ridiculous thing you have ever done?”

Either this question is going to shock you, or it's going to make you love how innocent they really are.

30. “What is something you used to do without thinking and now it embarrasses you?”

Time and taboos change, but the funniest moments are when you get caught missing the mark.

31. “What was the worst invention you ever heard of?”

If you have ever looked at old advertising, then you know there is some really oddball stuff that companies have tried to sell.

Other Good Questions to Ask Older People

Elder philosophy has a story inside every word. If you listen carefully, you might learn the keys to being happy without even trying when you come up with questions to ask old people.

32. “What did you learn about life?”

This is a great question to ask at the next family reunion. You may acquire enough knowledge in one afternoon to write a book. 

33. “Did you find the happiness you were looking for?”

You might find out that Grandma is still looking for happiness.

34. “Looking back, are you content with the choices you’ve made?”

At first glance, this can seem like a deeply personal question, but it may turn into something more philosophical.

35. “Do you have any advice on how to bounce back after hard times?”

This is potentially the most sage advice you’ll ever receive. 

36. “What experience(s) cemented your faith?”

This may not be a question an elder can answer. Still, it may bring up some conversations about living and experiencing life through the lens of religion.

37. “What does it take to be happy?”

Life is a journey, and along the way, an elder may have discovered that the key to happiness lies in the most obvious places.

Elder Advice

You'll learn more about life in one conversation with some elders than you ever expected. So, if the opportunity arises, don't turn down the chance to glean some incredible wisdom or a funny story.