Senior Emotional Health

What Grandpa Wishes You Knew About Him—100 Questions to Ask Him

What Grandpa Wishes You Knew About Him—100 Questions to Ask Him

In this article

There’s something Grandpa wants you to know. He was young once. And his walker doesn’t define him.

Chances are, he’d love it if you asked him about it. You might find you have a lot in common—or that your childhood lives were very different.

Either way, he’s probably got stories to tell.

Sadly, one of the most-read posts here at Frontida Assisted Living in Wisconsin talks about elderly depression. It’s not sad that people read it, but that so many seniors feel down. Often, it’s because life has changed so much that they might not feel like they fit.

  • Friends have passed on.
  • Landscapes have been altered.
  • Everything now needs a remote control.

But get Grandpa talking about the good ol’ days, and you might see a long-lost twinkle return to his eyes. Not to mention catching a glimpse of the young scoundrel he once was. And in time, he can see he still has something to offer. That his stories—and thoughts—are important, even if he’s older and living in an assisted living community.

Wondering if he can answer because he’s suffering from memory loss? Often it’s the new information that’s hard to recall because people with dementia aren’t storing new short-term memories.

But those long-term memories have had plenty of time to marinate, and talking about them at his memory care facility might help him process the “here and now.”

And if he can’t remember something? No biggie. Ask something different.

Need questions to ask? We’ve got 100 of them below. Some serious, some not so much.

If they spark ideas of your own, let us know on Facebook.

(And don’t forget you can permanently preserve Grandpa’s stories by recording him through the free app, StoryCorps, and uploading the recording to the Library of Congress.)

Frontida Assisted Living Facilities, such as the Kenosha’s Azalea Place, a Senior Living and Mental Health Community, provide you with posts like this one to help you live your best life.

Top” 100 Questions to Ask Grandpa

1. What did he play at recess?

2. What did he play on a rainy day?

3. First movie he ever saw in a theater

4. Favorite gift under the Christmas tree

5. Favorite gift he ever gifted

6. Does he have a scar? How did he get it?

7. Did he ever break a bone?

8. What was his best friend’s name in elementary school? Junior high? (because they probably weren’t middle schools back then) High School?

9. Favorite teacher? Least favorite?

10. Favorite class in school?

11. How did he get to school? (10 points if he says, “walked through five feet of snow, uphill, both ways”)

12. Did he take his lunch or buy it at school?

13. Something his dad taught him…something his mom taught him…

14. Favorite candy as a kid. Favorite candy now.

15. First job? Last job? Favorite job?

16. When he was little, what did he want to be when he grew up?

17. Did he ever meet someone famous? Did he ever shake hands with Sinatra? (for those Ocean’s Thirteen fans)

18. First crush.

19. First date.

20. How did he ask Grandma to marry him?

21. Where did they go on their honeymoon?

22. Favorite sport? Favorite board game?

23. Hardest thing he ever had to work for

24. First thing he saved up to buy

25. Something he wished he could go back and redo

26. Something he regrets doing…not doing….

27. What song makes him want to dance?

28. What does he like on a hotdog?

29. Favorite book as a kid

30. Favorite T.V. show

31. Favorite store to wander

32. Some place he visited with his family

33. Did he share a room as a child? Was he the neat or the messy one?

34. What fragrances take him back to his childhood?

35. When he was young, what did he do on Saturday mornings?

36. What time did he have to be at school?

37. Craziest thing he ever did for a school project

38. Where was he when he heard about Kennedy? The spaceship Challenger? 9/11?

39. Did he have pets?

40. Did he ride a big wheel?

41. Did he ever ride a horse?

42. A time when he got in a fight with a friend—and how they worked it out

43. Scariest thing he’s ever been through

44. What movie does he never tire of watching?

45. As a kid, did he like thunderstorms?

46. Did he ever build a snow fort?

47. Did he travel overseas?

48. Did he have to go to war?

49. What does he wish he learned to do?

50. Did he ever quit something? Did he ever not quit when he wanted to?

51. Something he always wished he’d told his children when they were young

52. Did he ever go to camp?

53. Did he ever go camping?

54. Thing he’s most proud of making, doing, or trying

55. Thing he wished he hadn’t tried

56. If he could do it all over again, what would he change?

57. What made Thanksgiving “Thanksgiving”? Christmas “Christmas”?

58. What meal felt like home?

59. What did he and his friends like to do in high school for fun?

60. What was something he tried to get away with—but got caught?

61. What were his chores growing up? Did he get an allowance?

62. Did he go to church? Does he have a favorite hymn?

63. Did he memorize Bible verses?

64. What was his favorite Bible story?

65. Was he the jock, the nerd, or the class clown?

66. Did he ever have to go the principal’s office?

67. Did he ever go to a costume party?

68. A memorable birthday

69. A memorable night

70. Did he ever get really lost?

71. How many years did he work at his job? What did he like most about it?

72. What was his first car?

73. Did he ever ride a skateboard? Scuba dive? Parasail?

74. Youngest memory that he has of his childhood

75. Saddest moment

76. Someone he always admired but never told them

77. When did he get his first computer? How big was it?

78. What were telephones like when he was young? TVs?

79.  was the dress code when he was in school?

80. What was the weirdest thing he’s ever eaten?

81. Where did he meet Grandma?

82. What’s his favorite of the 31 flavors?

83. How did he spend his summers as a kid?

84. How did a typical school day go?

85. Who does he wish he could see in concert?

86. Does he prefer winter or summer? The beach or the mountains?

87. Did he have cousins? Crazy uncles?

88. Did he have a nickname?

89. What was his school mascot?

90. Did he prefer climbing trees or walking around museums?

91. Were his parents strict?

92. Was he a city slicker or a country bumpkin?

93. Growing up, did he have to lock his front door?

94. What does he think is the neatest invention since he was little?

95. What changes in the world make him sad?

96. Did he have a mob full of friends or one or two side-kicks?

97. Was there a toy he always wanted but never got? Or finally got it and realized it was no good? (“You’ll shoot your eye out, kid.”)

98. Crunchy or creamy? Coffee or tea?

99. What color was his childhood house?

100. His favorite thing to do with his grandfather

Top 1000

Well, that 100 should prime the pump, not that Grandpa necessarily had to use one of those growing up. You’d have to ask him.

But you don’t have to stop there. Just think about something that was important to you when you were young and ask him if it was the same for him.

Soon you’ll forget the walker and see him for who he is—a man who lives. Loves. Learns.

And whose stories matter.

At Frontida Assisted Living in Wisconsin, we offer a plethora of assisted living services, including memory care and mental health care. We take a holistic approach to our senior living care, offering activities for seniors, wonderful accommodations and programs, and 24-hour supervision. We have dedicated memory and mental care centers and a team of compassionate caregivers who love what they do. Schedule a tour today!

Check out these other fun posts to learn more about your grandparents’ past.

A huge thank you to Kevin Gent and Mihai Lazăr on Unsplash for the featured photos

Elizabeth Daghfal
• 5 min read

Elizabeth Daghfal is a writer, teacher, speaker, and community volunteer. When she isn't teaching or writing-- Who are we kidding? Her husband and five kids say she's ALWAYS teaching and writing. She has a passion to help people who are struggling and is happy to say her shoulders are drip-dry. Born and raised in the South, she now lives in Wisconsin and loves it--except for the fifteen months of winter. Read more about her at