47 Questions That’ll Make Your Grandkids See You as a Kid Again

Is it weird that I imagine what it would be like to be friends with my grandkids when I was a little girl? (Don’t answer that…) Times have changed since we were little, but it is still fun to remind our grands that we were once their age and had our own interests and ways of doing things.

You know that I LOVE a good set of questions (do you see where I am going with this?), so I curated this list that allows our grandkids to see what we were like when we were their age. Have fun with these 🙂

After you ask, you can always reverse the question to make it about them too! Getting to know each other and remembering your past along the way is a wonderful bonding experience.

1. What do you think were my favorite toys as a child?
2. How do you think I spent my summers when I was your age?
3. Do you know what my first job was?
4. What kind of music do you think I listened to when I was a teenager?
5. Can you guess what I wanted to be when I grew up?
6. What was the most popular fashion trend when I was your age?
7. What type of hobbies do you think I had?
8. How do you think I met your grandfather?
9. What was my favorite book as a child, and why?
10. Do you know the name of my childhood pet?
11. Can you guess what I liked to do in my free time when I was your age?
12. What type of chores do you think I had to do?
13. What type of house did I grow up in?
14. Who was my best friend growing up, and why were we so close?
15. Can you guess my favorite food when I was a child?
16. How do you think I spent my weekends as a teenager?
17. What was my favorite movie growing up, and why?
18. Do you know where I used to go on vacation with my family?
19. Can you guess what type of student I was in school?
20. What were my favorite and least favorite chores growing up?
21. What was my favorite holiday tradition as a child?
22. Who was my role model when I was your age?
23. Can you guess what I loved to wear when I was your age?
24. What type of celebrations did my family have when I was young?
25. Can you guess what was my favorite subject in school and why?
26. Do you know what my favorite childhood TV show was?
27. How did I celebrate my birthdays when I was young?
28. Can you guess what the first car I drove was?
29. What was my most cherished childhood possession?
30. Can you guess what was the first concert I attended?
31. How do you think I did my homework before the internet?
32. What was my favorite family vacation and why?
33. Can you guess what was the most important lesson I learned from my parents?
34. Do you know what my first big purchase was?
35. How did I meet my first boyfriend/girlfriend?
36. What do you think I liked to do on Saturday mornings as a kid?
37. Do you know how old I was when I had my first crush?
38. Can you guess what my favorite playground game was?
39. What were the best and worst parts of school for me?
40. Can you guess what my first memorable achievement was?
41. How do you think I celebrated Halloween when I was young?
42. What do you think I did with my friends when I was your age?
43. Can you guess what my dream was when I was your age?
44. Do you know how my parents punished me when I misbehaved?
45. Can you guess what made me laugh the most when I was your age?
46. How do you think my life was different from yours when I was your age?
47. What do you think were my dreams and aspirations as a young adult?

Conclusion

These prompts are sure to kick-start some engaging conversations and help bridge the generational gap in a fun and interesting way! Let me know how it goes – I love hearing from you!