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27 Questions to Get to Know Your Grandparents

Grandparent and Grandaughter
My mother loved her grandfather, my great-grandfather, more than anyone and when he passed away she was heartbroken. One thing she always tells me is that she wished she asked him more questions about himself.  Like, “What was your childhood like?” My grandmother says the same thing about her relatives, wishing she asked more questions when they had time together. And now she feels it is too late. I take their advice every time I spend time with my grandma or other seniors in my life. I’ve learned to treasure my time, not take it for granted, in order to get to know my grandparents as deeply as I can.  By asking questions, I have learned that my grandpa was a karate champion. You just never know!  

Aging comes with unfortunate isolation and disconnection, but it doesn’t have to be that way! Here are 27 questions to ask your grandparent(s) to have them feel engaged and for you to get to know them better. You won’t regret forming a stronger connection. 


1. What was your career? 

2. What was it like being a stay-at-home mom?

3. How did you get into that career?

4. When did you know you wanted to do that? Did it just kind of happen? Do you miss it?

5. What was your childhood like?

6. What was your favorite thing to do as a kid?

7. Do you have any siblings?

8. What was it like growing up with those siblings? Are you still close? Who’s the oldest? Youngest?

9. What were you like in school? 

10. What were you most excited about when you graduated from high school / college?  Most worried about? 

11. What was your first job after college? 

12. What’s something you’re proud of? 

13. What’s something you regret?  Is there something you have been wanting to do, but holding yourself back because you did not want to do it alone? We can do it now!

14. Have your interests changed as you have gotten older?

15. What was the biggest change in your life, or the biggest life adjustment you had to make? 

16. Have you found your taste buds change as you get older?

17. What is the best trip you have taken?   

18. Do you have any hobbies? If yes, how did you find this hobby? If no, why not?  Want to find a hobby together?!

19. What has been the greatest discovery/ invention that you have witnessed in your life?

20. When did you first fall in love?  

21. (If married) When did you meet your spouse?  What was your first impression?

22 What do you remember about your wedding? 

23. What was it like having your first child?  What was the hardest thing, and the most joyful thing?

24. What is something you will never forget?

25. What is something you know that you want to pass on?

26. What are you most proud of in your life? 

27. If you could go back in time, would you change anything? 


Inspired by New York Times article “36 Questions That Lead to Love“.


Share your answers with us on Twitter @Hello_Mon_Ami!