Development Family

50 Questions To Ask Grandparents (Interesting, Insightful, Funny)

If you are lucky enough to have any grandparents, it can be a great idea to discover more about their lives, past history and worldly experiences by asking them a list of interesting questions.

It’s easy for young people to forget that older people were once young too, and have a wealth of stories, experiences and lessons that they can share with us all.

If you are interviewing your grandparents don’t be surprised if you learn a lot of amazing, interesting and funny things – but only if you ask the right questions and in the right way.

That’s easier said than done, so to go with our list of questions to ask your parents and siblings, let’s take a look at some of the best questions to ask your grandparents, as well as some tips and advice on how to get the most out of your interview.

50 Questions To Ask Your Grandparents


Yes, believe it or not, your grandparents really were once young!

So it’s a great idea to ask them questions relating to when they were a little boy or girl, and especially anything that relates to the age you are at now, as this will enable you can make immediate comparisons.

  • Tell me about your earliest memory?
  • Who was your favorite superhero growing up?
  • What sports did you play growing up?
  • What were your hobbies growing up?
  • Tell me about your best childhood friend?
  • What was your favorite childhood toy?
  • Did you have any pets growing up?
  • What do you remember most about your mother and father?
  • How did teachers discipline students when you were at school? Did you ever get caned (a form of corporal punishment when children were hit with a cane).
  • What technology do you wish was available when you were younger?


Things were probably quite different when your grandma and grandpa were courting, so this can be a fascinating area to delve into.

  • Was it love at first sight between you and grandma / grandpa? How did you know they were the one?
  • What’s the most romantic thing that grandma / grandpa has ever done?
  • What kind of activities did you do when you were dating?
  • How did you propose / be proposed to?
  • Tell me about your wedding.
  • Did you have a honeymoon / did you go traveling after getting married?
  • What’s the secret to a happy marriage?
  • What’s the most important thing to look for in a life partner?


Whether we like it or not many of us are heavily shaped by the work or daily activities we do, so this is another interesting conversational topic to explore with your grandmother or grandfather.

  • What was the best job you ever had?
  • What was the worst job you ever had?
  • How old were you when you had your first job?
  • How much money did you make at your first job?
  • Tell me about your best and worst boss? What made them so good / bad?
  • If you could have been anything in the world, what would it have been?
  • Do you think men and women should be paid the same amount?
  • Did people have a better work / life balance in the past?


There’s no doubt that travel was different many years ago, but that’s not to say people didn’t go on vacation or take trips.

From the places they’ve visited, to how they got there and the memories they made, asking your grandparents about past travels can be the gateway to a host of interesting stories.

  • What’s the most interesting place you’ve been to, and why?
  • What is your favorite city or country?
  • Tell me about anywhere that lived up to / didn’t live up to expectations.
  • What was it like traveling in the 50s, 60s, etc?
  • Tell me about your first car.

Life Advice

Most people who have been lucky enough to live a long life will tell you that one of the advantages is that they’ve seen their fair share of ups and downs, and along the way they have likely developed some valuable lessons and advice that they can pass on to younger people.

So take your time in exploring this area of questioning, because it can be extremely rewarding and fruitful!

  • What do you think is the secret to a long and happy life?
  • If you could live your life again, what would you do differently?
  • What is your biggest regret?
  • What is the bravest thing you’ve ever done?
  • What is the most stupid thing you’ve ever done?
  • If you could live during any period in mankind, when would it be?
  • Who do you most admire?
  • What’s the best book you’ve ever read?
  • What advice would you give your (insert your age) year-old self?


Lastly, our list wouldn’t be complete without some funny questions to ask your grandparents, such as:

  • What was life like before cell phones and the internet?
  • What’s the most embarrassing thing mom or dad did when growing up?
  • What’s your hidden talent?
  • Did you have a childhood nickname?
  • Can you tell me your favorite joke? Any joke in general?
  • Who is your favorite grandchild? Least favorite?
  • What is one thing most people don’t know about you?
  • What is your most and least favorite thing about being a grandparent?
  • If you could have dinner with your favorite movie character, who would you choose?
  • If you could have one superpower, what would it be, and why?

Tips on How To Interview Your Grandparents

Asking some interview questions for grandparents can seem a bit weird or forced, but it’s well worth it.

If interviewing is new to you, or you are not sure how to start, here are some tips and advice to help you on your way:

  • Listen well to your grandparent’s answers, and always be on the lookout for areas to probe and expand upon.
  • Ask open-ended questions to encourage your grandma or grandpa to open up their answer and invite greater storytelling and insights.
  • A good tactic can be to ask the easiest or more basic questions at the very beginning, as this will help relax both you and your grandparents.
  • Like any good reporter, if you are going to ask controversial questions then do so at the end in case things get a bit heated or emotional.
  • Remembering the 5W’s of journalism (Who, What, Where, When, Why) can help you with this assignment and in those times when you want to dig a bit deeper or probe for more information.
  • Finally, keep an open mind and respect that even thirty or forty years ago times were quite different, let alone double that length of time into the past. What was believed to be acceptable or right in past decades may now be perceived to be wrong, but people were dealing with the best information they had, so don’t judge the answers your grandparents give if these answers and views were shaped by the times they lived in.

Nick is a passionate dad who co-founded Rockinbaby to share his parenting journey with other new parents. He has a BSc and MBA, and works as a senior marketing professional. In his spare time Nick loves watching sports, staying fit and traveling. Learn more about Nick here.

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