170 Questions to Ask Your Grandpa: Childhood Memories to Life Advice

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Hey, grandkids! Looking to start an entertaining convo with your grandpa?

We all know that grandpas are like walking history books, filled with tales that will make your jaw drop and your imagination soar. 

Plus, many have a knack for infusing joy into every moment- from teaching us a new skill, sharing their favorite hobbies, or cracking jokes that make us burst into laughter, they remind us to embrace the lighter side of life and find joy in the simplest of things.

That’s why our list of questions to ask your grandpa will set the stage for some fascinating discussions and unveil the hidden gems of his extraordinary life.

From his childhood escapades that rival the wildest adventures to the timeless advice that only a grandpa can give, we have topics that got you covered.

So, find a cozy spot, prepare your grandpa’s favorite drink, and get ready to ask these questions.

Looking for more questions to ask grandparents? Try our fun questions to ask your grandmother.

Questions About Grandpa’s Childhood

Get ready to ignite the spark of nostalgia as we dive into your grandpa’s childhood. 

From his favorite games to his mischievous pranks, this set of grandparent interview questions will reveal interesting facts about his early years. 

1. How many siblings did you have?

2. Did you wear a lot of hand-me-down clothes?

3. Where did you live?

4. What type of house did you live in?

5. What meal did your mom make that you loved?

6. What type of meals did you eat?

7. Did you ever have to go without food?

8. Did you have chores as a kid?

9. What chore did you like the most, and which did you like the least?

10. Did your parents have a garden?

11. What was your favorite thing to play as a kid?

12. What kind of games did you play with your friends?

13. Did you collect anything?

14. What pets did you have?

15. What did your dad do for work?

16. Did your parents have a car?

17. Did you visit your grandparents a lot?

18. What is your first memory of school?

19. What was your most liked subject in school, and what was your least liked?

20. Did you ever get sick as a child?

21. How often did you see a doctor?

22. Did you go on many vacations?

23. Were holidays like Thanksgiving or Christmas a big deal?

24. Did you believe in Santa as a child?

25. What is your best childhood memory?

Santa sitting on a chair beside a fireplace surrounded by Christmas decor.

Questions About Grandpa’s Teenage Years

We’re about to dive into the teenage adventures of your grandpa, where first crushes, epic parties, and rebellious shenanigans were the name of the game. 

Get ready to hear tales that will transport you back to a time of unforgettable freedom, raging hormones, and youthful zest for life!

26. Were you a rebellious teenager?

27. Did you have a job, if yes, where was it?

28. Did you or your parents buy you your first car?

29. What kind of car did you drive?

30. What did you do in your spare time?

31. What high school did you go to?

32. Did you have a favorite teacher?

33. Did you spend much time in the principal’s office?

34. Did you graduate high school?

35. What kind of food did you learn to cook as a teenager?

36. What was your life like as a teen?

37. Did you date anybody as a teenager?

38. What kind of clothes did you wear?

39. Did you go to the movies a lot?

40. What was a past time you had that teens don’t do anymore?

41. Did you get along with your siblings?

42. Did you ever get into a fistfight?

43. Did you have your heart broken?

44. Did you go to any concerts with your friends?

45. Did your friends live close to you?

46. Did you play any musical instruments?

47. Were you part of any clubs at your school?

48. Did you ever run away from home?

49. Did you have a bicycle?

50. What type of hairstyle did you have?

51. Did you do your own laundry?

52. What is a luxury that we have now that you wish you had as a teenager?

53. Did you save up your money and make a big purchase as a teen, what did you buy?

54. What skill did you learn in your teenage years that you still use?

55. Did you ever protest anything? 

56. Are you still in touch with friends from when you were a teen?

Happy seniors clinking wine glasses while sitting on a table.

Questions About Grandpa’s Working Years

From his first job to his glorious career milestones, we’ll unlock the vault of professional experiences that have shaped your grandpa into the hardworking legend he is today. 

Prepare to uncover the secrets of success, funny office anecdotes, and other epic work stories!

57. How old were you when you started working?

58. How many jobs have you had?

59. What is the longest you have been at a job?

60. What was your favorite position?

61. What was your job title?

62. How many hours a week did you generally work?

63. Did you like working early in the morning, afternoon, or night shift?

64. Were you on your feet a lot at work?

65. Did you have a lot of paperwork to do?

66. Have you ever used a computer at work?

67. Would today’s technology have made your working years easier if it was available back then?

68. Did you have to wear a uniform at work?

69. Did you take lunch with you to work or get takeout?

70. What is something that an employer did that made you feel appreciated?

71. Did you like your boss?

72. Have you ever been angry about quitting a job?

73. Did you make friends with your coworkers?

74. Are you still friends with any coworkers?

75. Did you participate in potlucks at work?

76. How did you relax after work?

77. What did you like to do on your days off?

78. Did you need to go to university or college to get your job?

79. What is a career that you wish you would have had?

80. How old were you when you retired?

81. Did you have a retirement fund?

82. Did your work throw you a retirement party?

83. What was your least liked thing about working?

84. Do you miss working?

85. What do you think the best line of work is for young people to get into today?

Laptop on desk. Office. work.

Questions to Ask Grandpa About Family

It’s time to celebrate the bonds that tie us together- family!

The following questions for Grandpa will lead you through the intricate branches of your family tree, revealing tales of love and the moments that made your family truly special. 

86. How did you meet grandma?

87. How long did you and grandma date before you proposed?

88. How did you propose?

89. How long were you engaged before the wedding?

90. What drew you to grandma?

91. Where was your first date?

92. What was your most memorable date?

93. Who said “I love you” first?

94. Where did you and grandma buy your first home?

95. Did you have more or fewer children than you thought you would?

96. What kind of family vacations did you guys go on?

97. What pets did you and grandma buy for your children?

98. Did you have a lot of guests at your home?

99. Did you host the holidays or go to someone else’s house?

100. What were the summers like for your family?

101. What were some winter activities you liked to do as a family?

102. What was a hard situation that you and grandma went through together?

103. Did any of your children get really sick while growing up?

104. What types of meals were family favorites?

105. Did you always have your kid’s friends at your house?

106. Did you watch any shows together as a family?

107. Did your kids play sports?

108. Did you enjoy taking your family to sporting events?

109. Where did you guys shop for clothing?

110. Did you take a lot of pictures of your family?

111. What kind of car did you drive during those years?

112. Did you move around a lot with your family?

113. Do you still keep in touch with people you met from family vacations?

114. Did you go to any school plays?

115. Were you or grandma involved in your children’s school?

116. Was money tight while raising your family?

More family-oriented conversation starters in our guide to questions to ask your dad, and mom.

Happy senior couple talking in a family dinner while holding wine.

Questions to Ask Grandpa About Funny Stories

It’s time to loosen those funny bones and share a hearty chuckle with your grandpa. 

These questions will unlock the side-splitting stories that will have you rolling on the floor with laughter. 

117. Have you played pranks on grandma?

118. Have you backed up someone’s toilet recently?

119. Do you have any funny nicknames for grandma?

120. What was it like in the dark ages, aka before cell phones and the internet?

121. What was the most embarrassing thing one of your kids did growing up?

122. What was something funny that my mom/dad did that you had to punish them for?

123. Can you show me your best dance move?

124. Do you know what twerking is?

125. What is your favorite joke?

126. If you could be in any cartoon, which would you pick and why?

127. What is a food that makes you want to vomit?

128. What is something that always makes you laugh?

129. Do you have a social media account?

130. Do you have any hidden talents that you are embarrassed by?

131. Have you been kicked out of anywhere for any reason?

132. What is the funniest thing you have seen me do?

133. What is the weirdest fashion trend you have ever tried?

134. What is the weirdest food you have ever eaten?

135. Have you flipped off a little kid?

136. Have you been kicked out of somewhere for being too drunk?

137. Have you been really drunk recently?

138. Have you broken the law?

139. Has grandma broken the law?

140. What is the most annoying thing about grandma?

141. Have you ever been in public and embarrassed grandma?

142. Am I your favorite grandchild?

Grandfather and granddaughter talking to each other while sitting.

Questions to Ask Grandpa About Life Advice

Grandpa’s wisdom is a gift that keeps on giving! 

In this final round, prepare to receive lots of life advice straight from the source. 

From love and success to resilience and happiness, these grandparent interview questions will unveil the invaluable lessons your grandfather has learned along the way. 

143. What do you believe is the secret to a long and happy life?

144. If you had the chance to do something over again in your life, what would it be?

145. What is something you deeply regret?

146. What is a chance you wish you would have taken?

147. What is the bravest thing you have done?

148. What advice did your parents give you that you want to pass on to your children and grandchildren?

149. What is the biggest piece of relationship advice you have to offer me?

150. What is something you think everyone should invest in?

151. What valuable life lesson did you learn that took you a while to learn?

152. What are some things you did over the years to find peace?

153. At what point in your life did you start to feel fulfilled?

154. What is more important, making money or cultivating peace?

155. What is a lesson you have learned about trust?

156. Do you think having a daily routine is key to success?

157. Do you believe that sleep is important to the overall quality of life?

158. What would you say to someone who is looking for love?

159. Do you have tips for people raising young children right now?

160. What is something you feel you did wrong raising your children?

161. What is something you feel you got right raising your children?

162. Do you think education is important?

163. How did you handle balancing the demands of your family life and your work life?

164. Do you think it is important for someone to have a mentor?

165. Do you think it’s important for someone to volunteer their time?

166. What is the key to staying youthful?

167. Is being grateful an important part of being happy?

168. Can you trust someone who has lied to you once?

169. How much grace should you show people?

Happy grandfather and grandson sitting on a tree trunk in a forest.

Final Thoughts

Did you have fun with our grandpa questionnaire?

Let us know in the comments what question sparked the most interesting conversation! 

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