50 Questions to Ask Your Grandparents That’ll Pull the Curtain Back on Their Lives

Demystify your grandparents, one question at a time.

Published June 28, 2023
Young woman talking with her grandmother

There may come a time for when you try to recall a story your grandparents told you, but you've forgotten some of the important pieces and they're not around to ask. But, whipping out your phone to record every conversation you have with your grandparents isn't the solution to problem. Instead, make a conscious effort to ask important and insightful questions to them while they still remember.

Need help guiding your convos? We've got all sorts of awesome questions from serious to silly that you can ask them.

Nostalgic Questions to Ask Your Grandparents About Their Childhood

As you think back on your own childhood, the memories just start flowing. Unlock those long-forgotten moments from your grandparent's childhood by asking the these nostalgia-inducing questions:

  • What do you remember thinking was a really expensive price when you were a kid?
  • As a child, what were your everyday responsibilities?
  • What were my grandparents like as parents?
  • What's the biggest difference you see between the way kids are raised today and the way you were raised?
  • What was the biggest news headline you remember as a kid?
  • Did you experience any near-death experiences when you were young?
  • What did you think you were going to be when you grew up as an elementary schooler?
  • Did you ever sneak out? And did you get caught?
  • What task that's now automated do you miss doing the most?
  • What was your favorite hobby as a kid?
  • What was the best birthday you ever had?
  • What's your funniest memory from your time in school?
  • What was your childhood best friend like?
  • Can you describe what your first job was?
  • What was your childhood neighborhood like?
  • When you think about the happiest memory from your childhood, what comes to mind?
Quick Tip

Use little moments to ask your grandparents questions. If they're into quilting or gardening now, use that as a lead-in to ask about what they were interested in as a kid. Ask about favorite childhood dishes during a meal, or what their childhood home was like as you're taking a walk around the neighborhood.

Funny Questions to Ask Your Grandparents About Their Lives

Not everything you ask your grandparents has to be heavy, life-changing stuff. Sometimes the best pieces of advice come from the wildest asides. If you want to keep things light, skip the formal interview questions and see your grandparents in a whole new light by listening to their responses to these silly questions.

  • What's the largest amount of money you wasted on something stupid?
  • (If they invest) What's the worst stock you ever invested in?
  • Looking back, what's one embarrassing memory you still cringe at today?
  • Have you ever gotten in trouble with the law?
  • Imagine both are readily available - which would you choose, manual or automatic transmission?
  • What's your "back in my day" pet peeve?
  • What fashion fad do you never want to have a comeback?
  • Did soda taste better when soda jerks used to make it?
  • If you could bring back one article of clothing from your past (and it magically fit today) what would it be and why?
  • What's one discontinued snack food you'd pay big money to taste again?
  • What's the wildest job you ever took?
  • Did you ever let loose and have wild night out?
  • Who was your first celebrity crush?

Serious Questions to Get Your Grandparents' Wisdom

Your grandparents have lived full, adventurous lives, and it'd be a waste not to get their wisdom before they're gone. Use these questions to delve deep into their lives:

  • Who do you regret losing touch with the most?
  • Is there a life-changing moment in your life where you think you made the wrong choice?
  • When you think of home, what comes to mind?
  • Do you think there's a defining moment in your life that impacted who you've become today?
  • Do you have a "the one who got away" story?
  • Which deceased family member do you remember the best?
  • What's your favorite piece of relationship advice?
  • What's a habit you wish you'd quit earlier?
  • What are the stories behind our family heirlooms?
  • Do we have any family scandals, and if so, what are they?
  • What decade of your life (20s, 30s, 40s etc) was the worst?
  • What decade of your life was the best?
  • Are there any major accomplishments you haven't made that you really want to?
  • What conversations do you regret not having with your parents?
  • What are the choices you're most proud of?
  • If you could do it all differently, what's one thing you'd like to change this time around?
  • Is there something you were ashamed about yourself that you wish you'd accepted earlier on in life?
  • What's one thing you could never talk to your parents about?
  • What are your thoughts on love?
  • What's the thing you hope for the most concerning my future?
  • When buying or decorating a new home, what's your number one piece of advice?

Ways to Spark a Conversation With Your Grandparents

With such a large age gap, your grandparents can sometimes feel more like monuments than real life people. For years, they're shrouded in mystery, a blank canvas there to love and support you without a story of their own. As you get older, you might start seeing them more as the seasoned adults they are, with entire lives full of mistakes, accomplishments, and hilarious stories.

But, some grandparents are more forthcoming than others. So, here are some ways to crack through their shells and ask the hard-hitting questions you're dying to know the answers to:

  • Ask them to teach you one of their favorite hobbies. This may seem off the wall, but if you show interest in one of their hobbies, you're creating an environment they feel safe, comfortable, and in control of. Then, when you ask personal questions, they'll be more open to responding to them.
  • Start by asking questions about raising your parent. Talking about your parents is a great way to bridge the gap because they're your shared middle ground. After a while of you all talking, you can start branching out the conversation to centering on your grandparents as people rather than just as parents.
  • Gauge how comfortable they are by asking easy questions first. Don't start in with the hard-hitting journalism if you're not positive it's going to be received well. Instead, gauge how comfortable they are with talking about their past by asking silly questions that aren't too personal first.
  • Prompt them to talk about their childhoods using photos. If you're over at their house and you see old pictures of them as kids or family members you dont' recognize, you can point to them and ask your grandparent's who that is. It's a way to spark a conversation about the past that's not abrupt.

How to Record Your Grandparent's Responses

You don't have to have a massive podcasting set up just to record your grandparent's responses to these questions. All of them will get the job done, but which one you like the most depends on your grandparents, your tech knowledge and access, why you're asking them questions, and whether you're hosting an interview session or just asking a question in passing.

  • Keep a running file in your notes app on your phone. This is the quickest way to write down the answers of a one-off question.
  • Record them using voice notes. Voice notes are the 21st century version of the tape recorder, and can give you a more personal touch to the responses.
  • Go old school and record them on tape. If you want the physical vibe of retro reporting, consider getting a tape recorder and actually recording them. And while carrying around tapes is a hassle; the upside is it's harder to accidentally delete a tape than a digital file.
  • Screen record your video calls. If you don't live close by and can't visit, you can still compile all of their answers. Simply screen record any video calls or chats you have on your phone or your computer.

Your Grandparents Won't be Around Forever

It doesn't matter how many wishes you make on your birthday candles; your grandparents aren't going to be around forever. Instead of wasting time ignoring that fact, make the effort to ask the questions your curious about and learn about who they are as people. And since grandchildren hold a special place in their grandparent's hearts meaning, there'sprobably not a question you could ask that they won't try to indulge.

50 Questions to Ask Your Grandparents That’ll Pull the Curtain Back on Their Lives