50 Nostalgic Questions That Will Make Your Grandkids See You in a New Light

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You have asked your grandkids more questions than you can count (isn’t it fun?), and now it is time to turn the table and ask them questions about YOU! Don’t worry – you don’t have to tell them about that weekend-long music festival you attended in the 70s (Willie Nelson was the headliner – need I say more?), but rather things about your interests and passions! If you are ready to unlock your own memory box, here are 50 age-specific questions to get the ball rolling:

Toddlers (2-4 years old):

Grandmother and grandchild
  1. Do you know what Grandma’s favorite color is?
  2. Can you guess what grandma’s favorite animal was when she was your age?
  3. What kind of toy do you think Grandma liked to play with?
  4. Do you know what Grandma’s favorite game was?
  5. Do you know where Grandma used to live when she was little?
  6. Do you know what Grandma’s job used to be?
  7. What kind of games do you think Grandma used to play as a little girl?
  8. Can you guess what kind of food Grandma loves the most?
  9. Do you know what Grandma’s favorite holiday is?
  10. Do you know what Grandma’s favorite movie is?

Pre-School (5-6 years old):

Out the door to start a great day

11. Can you guess Grandma’s favorite book when she was your age?
12. What type of food do you think Grandma loved most as a child?
13. What do you think Grandma wanted to be when she grew up?
14. What kind of music do you think Grandma liked to dance to when she was your age?
15. Can you guess Grandma’s favorite childhood movie or TV show?
16. Can you guess what Grandma’s favorite childhood memory is?
17. Do you know what makes Grandma laugh the most?
18. What do you think was Grandma’s favorite vacation she ever took?
19. Do you know Grandma’s favorite season of the year?
20. Do you know where Grandma was born?

Elementary School (7-10 years old):

Reading a book together

21. Do you know what subjects Grandma liked best in school?
22. Can you guess which sports or hobbies Grandma was into?
23. What kind of chores do you think Grandma had when she was your age?
24. Do you know what Grandma had for her first pet?
25. What do you think that (pet) was named?
26. What do you think Grandma used to do in the summer?
27. Can you guess what Grandma’s favorite ice cream flavor is?
28. Can you guess what Grandma’s favorite thing to cook or bake is?
29. Do you know how Grandma and Grandpa met?
30. Can you guess where Grandma would love to travel if she could go anywhere in the world?

Middle School (11-13 years old)

Sharing the iPad on the floor

31. Can you guess what the coolest piece of technology was when Grandma was your age?
32. What was Grandma’s favorite book or book series in middle school?
33. Can you guess Grandma’s first job and what she bought with her first paycheck?
34. What were Grandma’s favorite band and type of music in middle school?
35. Can you guess what fashion trends Grandma followed when she was your age?
36. Can you guess who Grandma’s childhood hero was?
37. Can you guess Grandma’s favorite hobby?
38. Do you know what Grandma’s favorite song is?
39. Do you know who was Grandma’s first best friend?
40. Can you guess what was Grandma’s first car?

High School (14-18 years old):

Family photo on a giant chess board

41. Do you know who Grandma’s best friend was in high school and a fun adventure we had together?
42. Can you guess what car Grandma drove or wanted to drive in high school?
43. What kind of clubs or sports was Grandma involved in during high school?
44. Can you guess what prom or homecoming was like for Grandma?
45. Do you know what Grandma’s dream was when she was in high school?
46. Do you know what historical event had the biggest impact on Grandma when she was young?
47. Do you know what Grandma studied in college or what she wanted to study?
48. Can you guess what was the first concert Grandma ever attended?
49. Can you guess what Grandma’s favorite family tradition is?
50. Do you know what Grandma considers to be her greatest accomplishment?

Conclusion

Remember, the goal of these questions is to engage your grandchild in a fun way while also sharing a bit of your own history and experience. It’s not a quiz, it’s a conversation starter, so have lots of fun with it! If you haven’t already, be sure to also check out my other questions for grandkids.

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