100 Questions to Ask Your Dad

Here's a thing about dads: ask "how are you?" and you get "fine." Ask "what was your first car?" and forty-five minutes later you know about the summer of 1987, the friend who talked him into buying it, and the girl he drove it to see. The right questions to ask your dad are almost never head-on — they're side doors. Ask about the car, the job, the game, and the life comes with it.

These 100 questions are built on that principle. They start with things any dad enjoys talking about, and they end at questions most fathers spend their whole lives waiting to be asked — even if they'd never admit it.

How to use these questions

Don't announce an interview. Ask one in the car, at the grill, on a Sunday phone call. The list is ordered gentle to deep on purpose — early questions build the habit of him talking, later ones use it. And keep the answers somewhere: write them down after, or record a voice memo while he talks. His voice is part of the story.

Questions to ask your dad about his boyhood

Every dad was a kid with scraped knees and a scheme. These are the easiest questions on the list, and they're where the storyteller in him wakes up.

1. What kind of kid were you — quiet, wild, funny, always in trouble?
2. What did a summer day look like for you at ten years old?
3. What was your neighborhood like — who were the characters on your street?
4. What's the best toy or bike or contraption you ever owned as a kid?
5. What did you and your friends build, break, or almost get away with?
6. Who taught you to ride a bike, throw a ball, or use a tool — and how?
7. What smell or sound takes you straight back to being a boy?
8. What was your family's dinner table like when you were growing up?
9. What did you save up forever to buy as a kid — and was it worth it?
10. What scared you as a kid that you never told anyone about?
11. What was your first pet, and what happened to it?
12. What's a place from your childhood you wish you could walk through one more time?

School, mischief, and first freedoms

The teenage years are where dads keep their best material — and their most surprising selves. You may not recognize the person in these answers.

13. Were you a good student, or good at looking like one?
14. What's the most trouble you ever got into at school — and was it worth it?
15. Who was your favorite teacher, and did they know what they meant to you?
16. What was your first car, and what did it cost you — in money and in repairs?
17. Where did you go the first time you drove somewhere alone?
18. What music did you blast when nobody could tell you to turn it down?
19. What did you look like at seventeen — clothes, hair, the whole picture?
20. What's something you did as a teenager that your parents never found out about?
21. Who was your best friend back then, and what did you two get up to?
22. What was your first date ever — where did you go and how did it end?
23. What did you think your life was going to look like when you were eighteen?
24. When did you first leave home, and what did that first night away feel like?

Work, money, and what he built

For a lot of fathers, work is where the pride and the sacrifice live — and where nobody thinks to ask. These questions honor that without making a speech about it.

25. What was your very first job, and what did it pay?
26. What did you do with your first real paycheck?
27. What's the hardest job you ever had — and what did it teach you?
28. Which boss or coworker changed how you saw yourself — and how?
29. What's a piece of work you're still proud of, even if nobody remembers it but you?
30. Did you ever want a completely different career? What happened to that dream?
31. What was money like when I was little — were there hard years I didn't know about?
32. What's the best purchase you ever made, and the worst?
33. What's something you fixed, built, or made with your hands that mattered to you?
34. What did your father teach you about work — and did you agree with him?
35. Which fork in your working life changed the most — and did you know it at the time?
36. What do you wish someone had told you about work when you were twenty?

The loves of his life

Ask what really happened — not the anniversary-toast version. If your parents are together, there's a story you've never heard all the way through. If they're not, there's an even more honest one.

37. How did you actually meet Mom — what really happened, start to finish?
38. What was it about her that made you fall in love?
39. What was your first date with her like — and were you nervous?
40. When did you know it was serious?
41. What do you remember about your wedding day that isn't in the photos?
42. What's the hardest thing you two ever went through together?
43. What did you learn about love the hard way?
44. Who was a love before Mom that shaped you — and what happened?
45. What does love look like at your age that it didn't at mine?
46. What's one thing about marriage you'd want me to know that nobody says out loud?

Becoming a dad

Fathers rarely narrate this part of their lives — the terror and the joy of it. Give him the chance. These answers tend to be the ones that stay with you.

47. What did you feel the day you found out you were going to be a father?
48. What do you remember about the day I was born?
49. What terrified you most about being a new dad?
50. What kind of father did you promise yourself you'd be?
51. What's something your own dad did that you swore you'd do differently?
52. What's something he did that you ended up doing anyway?
53. What's a moment with me when you were proudest — one I probably don't know about?
54. What's a moment when you felt like you'd failed as a dad — and what would you tell yourself now?
55. What was the hardest age to parent me, honestly?
56. What did you give up to raise us that you've never mentioned?
57. What did having kids teach you that nothing else could have?
58. What do you hope I do differently with my own kids someday?

His people

Behind most dads there's a best friend from forty years ago, a mentor, a brother, a hero. These questions bring those people into the room.

59. Who's the best friend you've ever had, and where are they now?
60. What's a friendship you lost that you still think about?
61. Who did you look up to most when you were becoming a man?
62. Which of your siblings knows you best — and what would they say about you?
63. What's the most fun you ever had with your brothers, sisters, or cousins?
64. Who showed up for you in a hard season when you didn't expect it?
65. Who do you wish you'd thanked properly — and what would you say now?
66. Who made you laugh harder than anyone in your life?
67. What did your mother mean to you — in words you've never used out loud?
68. If you could have one more conversation with anyone who's gone, who would it be?

The things he doesn't say out loud

Every father carries a version of himself nobody asks about. These questions ask. Go slowly here, and let the silences do their work.

69. What's something you're proud of that you've never once bragged about?
70. What's a fear you carried for years that I never knew about?
71. What's the hardest thing you've ever lived through?
72. What's a regret you've made peace with — and one you haven't?
73. When was the last time you cried, and what was it about?
74. What do you miss most about being young?
75. What's something you always wanted to do and never got the chance to?
76. When have you felt most alone — and what got you through it?
77. What's a compliment you received once that you never forgot?
78. What part of your life do you wish someone had asked you about before now?
79. What's something about you that you think I've got completely wrong?
80. What would your eighteen-year-old self think of the man you became?

What he knows now

A dad's advice hits different when you ask for it instead of receiving it unsolicited. These questions go looking for the lessons he actually paid for.

81. What's the best decision you ever made, and did it feel like it at the time?
82. What's the biggest risk you ever took?
83. What do you know about handling failure that took you decades to learn?
84. What's the best advice your father ever gave you — and did you take it?
85. What advice do you find yourself wanting to give me that you hold back?
86. What should I absolutely not waste my time worrying about?
87. What makes a man a good man, in your book?
88. What's a belief you held hard when you were my age that you've let go of?
89. How do you want to spend the years you have ahead of you?
90. What does enough look like — money, success, all of it?
91. What's the secret to the friendships and marriages that last?
92. If you could teach me one skill you have before it's lost, what would it be?

The tender ones

Save these for the right moment. A quiet porch, the end of a visit, the last hour of a long drive. These are the questions people wish they'd asked — ask them while the asking is easy.

93. What do you want me to remember about your parents, so they're not forgotten?
94. What's a story from your life you've never told me that I should know?
95. What are you most grateful for, when it's all added up?
96. What do you hope people say about you when you're not in the room?
97. What's one thing you want me to promise you?
98. What was the best day of your life — the honest answer, not the expected one?
99. What do you hope my life looks like when I'm the age you are now?
100. What do you most want me to remember about you?

How to keep him talking

• Do something while you talk. Drive, fish, cook, fix a thing. Eye contact optional; motion helps.
• Trade stories. Answer the question yourself first sometimes. It stops being an interview and starts being a conversation.
• Don't rush the pause. He's not done — he's deciding whether to tell you the real version.
• Follow the objects. The watch, the toolbox, the photo in the garage. Every object he's kept has a story attached.

One question at a time

Nobody asks their dad a hundred questions in a sitting — and honestly, you shouldn't try. The version of this that actually works is one question, asked casually, again and again over months. That's the entire idea behind GetToKnow: your family gets one question a day, Dad answers in his own words — typed or spoken — and every answer is saved in a private family archive for good.

And when you've heard his answers, don't stop with him. Your mom has a hundred stories of her own — start with these questions to ask your mom — and if you're lucky enough to still have grandparents, don't wait on these questions to ask your grandparents.