Father’s Day is Sunday. Celebrate all that your father means to you. Perhaps he’s your teacher, protector, support system, or even your best friend. His legacy is one you’ll never want to forget. How do you make sure it’s honored?
It starts with asking good questions.
This year, give Dad the gift of your curiosity. Ask him questions about his life—the ones you don’t know the answer to. Be intentional while you have the opportunity. Lean in and listen to what he has to say.
Below, we’ve compiled a list of 100+ questions to ask Dad this Father’s Day. Write your favorites—or all of them!—in a Leatherpress notebook, and leave room for his answers. Gift him the notebook and schedule time to interview him. You can transcribe his responses as he talks, or better yet, he can write the answers himself so his thoughts are recorded in his own handwriting.
If you want to complete all hundred questions, consider answering only a handful a day over the course of a few weeks. Hopefully you’ll discover lots of new facts about your dad—some fun, some funny, and many kernels of wisdom. You’ll never regret getting to know him better.
100+ Questions to Ask Your Dad This Father’s Day
About his Childhood
1. Where were you born?
2. Where did you grow up?
3. If you moved houses as a child, which one was your favorite—which felt most like home? Why? What do you remember most about it?
4. Where did you go to school?
5. What were your teachers like? Did you have a favorite? How about a least favorite? Why?
6. What subjects interested you the most in school (even if that was recess!)?
7. Did you enjoy all your classmates, or were there some you just didn’t like?
8. What was your mother like? What lessons did you learn from her (consciously or not)?
9. What was your father like? What lessons did you learn from him (consciously or not)?
10. If you had siblings, what was your relationship like with each of them growing up? If you were an only child, what was that like for you?
11. What imagery or feelings would the word “family” have brought to mind as a child? Is it the same for you now?
12. What is your earliest memory as a child?
13. What is your happiest memory as a child?
14. What is a memory from your childhood that shaped you significantly, for better or for the contrary?
15. Were you insecure about anything as a child? Why?
16. Picture your childhood as a patchwork quilt. What would it be made of—what smells, scenes, textures come to mind?
17. How did you enjoy spending your time the most as a child? What activities made you feel truly like yourself?
18. Describe yourself as a child in five words. Do you feel any of these are still true of you today?
19. Who was your best friend(s) and why? What are your favorite memories with them? Are you still in contact?
20. If you could have had any superpower as a child, what would it have been? Why?
21. Did you have a favorite trip or vacation spot? What made it so special?
22. Did you have any childhood pets? What were their names? What are your fondest memories with them?
23. What did you hope to be when you grew up?
About his Teenage Years
24. What memory stands out to you the most as a teenager?
25. What was your favorite memory from your teenage years?
26. Describe yourself as a teenager in five words. How did those compare to how you described your childhood self?
27. What was an insecurity you had as a teenager?
28. How did your friendships shift as a teenager?
29. How did your relationships with your family shift as a teenager?
30. How did your sense of self change as you became a teenager?
31. What was the biggest lesson you learned about friendship as a teenager?
32. What was the biggest lesson you learned about life as a teenager?
33. What’s a decision you regret about your teenage years?
34. What’s a decision you’re glad you made?
35. What’s a decision you believe you wouldn’t be where or who you are today without?
36. What social or cultural influences shaped you the most as a teenager?
37. Did you have school dances? What were they like? What did you wear? What memories of or feelings from them stand out to you the most?
38. What is your strongest memory of high school?
39. What subjects did you like studying the most in high school? What were your least favorite? Did you ever fail a test?
40. Who was your favorite high school teacher? Who was your least favorite? Why?
41. What classmates did you enjoy? Were there any you didn’t?
42. How did you feel about learning to drive? What kind of a driver were you? Did you ever receive any speeding tickets?
43. What did you learn about relationships as a teenager?
44. What were trends (clothing, hair, music, room decor, or otherwise) like as a teenager? Did you align with them, try to pave your own path, or both?
45. What is the biggest lesson you learned from your teenage years?
About his Young Adult Years
46. How did your perspective on life shift as a young adult?
47. How did your friendships shift as a young adult?
48. How did your relationships with your family shift as a young adult?
49. Did you go to college? If so, describe your experience in a few words. Where did you go and what did you study? Did you enjoy it? Why?
50. Are there any professors who stand out to you from college?
51. If you didn’t go to college, what path did your life take? Do you regret or appreciate your decision now? Did you feel the same in the moment?
52. What were a few of your most impactful memories from your young adult years (whether college or beyond)?
53. How did you feel trying to launch your career? What was that process like?
54. Did you start with a job you enjoyed, or simply one that paid the bills? What did you learn from that phase of life?
55. How did your sense of self change as you became a young adult?
56. What life lessons have stuck with you from your young adult years?
57. What are you the most grateful for as you reflect on your young adult years?
About Parenthood
58. How old were you when you became a dad?
59. How did you feel about becoming a dad?
60. How did your perspective on life shift as a parent?
61. How did becoming a dad shape who you are today?
62. What is the biggest lesson you learned from parenthood?
63. Do you remember the day I was born? What was it like? What about my siblings?
64. How was parenting me different from raising my siblings?
65. What is the most humorous memory you have of me as a child?
66. What is the most vivid, impactful, or meaningful memory you have of me as a child?
67. What was something you struggled the most with as a parent?
68. Do you feel you reflected your father’s parenting style, or were you different?
69. Is there anything you would do differently as a father, looking back?
70. What example did you hope to set as a father?
71. How did becoming a dad transform your relationship with your own father?
72. What is something you appreciate most about fatherhood?
73. How would you describe me as a child in five words? Are those words similar to the way you would have described yourself as a child?
74. How did becoming a dad “connect” you with your younger/childhood self?
75. Is there anything you learned from me as a child?
About his Later Adult Years
76. What is life like now that I, as your child, am an adult?
77. If you’re empty nesting, what has that been like? What has been challenging? What has been rewarding?
78. As you look back on your life at this point, is there anything you wish you’d done differently?
79. What is one decision you’re incredibly grateful you made?
80. Did you accomplish some of the things you hoped to in life?
81. What was the biggest curveball life has “thrown at you” so far? How did you handle it? What might you do differently today? What did you learn from it?
82. How have you enjoyed your career over the years? What are some of the challenges it offered you? How did those shape you as a person?
83. What are you most grateful for about your career? What about your coworkers—are there any you appreciate or have learned from?
84. Did you have any pets as an adult? What were they like? Did you enjoy having them?
85. What was the biggest bucket list item you’ve checked off? Are there any you’d still like to complete?
86. If you could choose a few days to relive from your life so far, which ones would they be and why?
87. At this point in your life, what would your ideal day be? Who would it be spent with? What would you be doing?
88. Who are some people that have impacted you the most over the years—perhaps a role model you have looked up to? Why?
89. Describe yourself now in five words. Are they similar to the ones you’ve used for previous stages of life? Why do you think that is, or why not?
90. How have your hobbies and interests changed over time? Have you gained new ones? Reconnected with (or lost) old ones?
91. How has your sense of self changed over the years to become who you are today?
92. What is the best piece of advice you’ve received in life?
About His Values & the Legacy He Hopes to Build
93. What are some of the biggest life lessons you’ve learned so far?
94. If you could change one thing about your life at this moment, what would it be? Why?
95. What are your moral or religious beliefs? How have those changed or been shaped over the years?
96. What is your perspective on the meaning of life?
97. What ultimate purpose do you feel your life has served so far?
98. What qualities or virtues do you esteem the most? Do you feel your life reflects that esteem?
99. How have your values changed over the years?
100. What do you hope to accomplish going forward in life? Why?
101. If people remembered your name 100 years from now, what would you hope it was for?
We often forget our fathers were once our age, in our shoes, navigating the uncertainties of life just as we do. As your dad answers these questions, we hope you discover new and unexpected sides to him that will strengthen your relationship—lessons you can learn from and stories that will deepen your appreciation for him.
Don’t forget to shop our Leatherpress journals to preserve his answers in a safe place and cherish his legacy for decades.