50 Questions to Ask Your Dad (Funny, Deep and Easy to Start)

A lot of dads are not big on long heart-to-hearts. They show up, fix things, drive you places and make the same jokes for twenty years. That can make it hard to know what is going on in his head, and just as hard for him to know what is going on in yours. A few good questions can change that, without anything feeling awkward.

Here are 50 questions to ask your dad, from easy icebreakers to ones that lead to real conversations. Use them in the car, while cooking, at a game or on a phone call. You do not need to ask them all. Pick the ones that make you curious.

Tips for getting your dad talking

• Do something together first. Many people talk more easily side by side than face to face. A drive, a walk or a project in the garage is perfect.
• Start light. A funny question builds trust before the deeper ones.
• Be patient with silence. He might need a minute. Don't rush to fill it.
• Share your own answer. It turns an interview into a conversation.
• Keep what he tells you. Write down the good stories or ask whether you can record them.

Funny and easy questions to ask your dad

1. What is your best dad joke, and where did you get it?
2. What is the worst haircut you ever had?
3. What was your first car, and what was wrong with it?
4. If you had to eat one meal for the rest of your life, what would it be?
5. What was the first concert or big event you went to?
6. What is your most useless talent?
7. What movie can you watch over and over?
8. What is the funniest thing I did when I was little?
9. Which of your habits drives everyone else crazy?
10. If you could be great at any sport instantly, which would you pick?

Questions about his childhood and youth

11. What was your favorite thing to do as a kid?
12. What was your school like, and what was your favorite subject?
13. Who was your hero growing up?
14. What did you want to be when you grew up?
15. What chores did you have, and did you hate them?
16. What did you do for fun on weekends and holidays?
17. What is a family story that nobody tells enough?
18. What was your best friend like back then?
19. What is your best memory with your own dad?
20. What is something you got in trouble for as a kid?

Questions about work, money and growing up

21. What was your very first job?
22. What job did you like the most, and why?
23. What is the best money lesson you have learned?
24. What skill do you wish you had learned earlier?
25. What was the hardest decision you ever made at work?
26. If you could try a completely different career, what would it be?
27. How do you deal with stress?
28. What do you think young people today get right?
29. What do you think young people today have it harder with?
30. What is something you are still learning?

Questions about being a dad

31. What was it like when you found out you were going to be a dad?
32. What surprised you most about being a father?
33. What is your favorite memory of us together?
34. What are you proudest of as a dad?
35. Is there something you wish you had done differently?
36. What did you want to teach me most?
37. What do you worry about when it comes to me?
38. What is the best advice you have ever received?
39. What would you tell your younger self?
40. What do you hope I always remember?

"How well do you know me?" questions for your dad

Turn it around and see how much he knows about you now. These ten questions are the heart of a dad quiz.

41. What is my favorite thing to do with you?
42. What is my favorite sport to watch or play?
43. What kind of music do I listen to most?
44. What was my favorite toy as a kid?
45. What would I do with an unexpected free day?
46. What is my best skill?
47. What do I worry about most?
48. What cheers me up fastest?
49. What is my worst habit?
50. What kind of house would I want some day?

Make it a game: the dad quiz

If you want to see how he does on those last ten, try our free Dad Quiz. You answer 10 questions about yourself, get a link and send it to your dad. He guesses what you picked, and his score appears on your scoreboard. Mom, siblings and grandparents can take it too, so you can see who knows you best.

Looking for something similar for other family members? We also have a list of questions to ask your mom and questions to ask your sister.

One last thing

The goal is not to get perfect answers. It is to let him know you are interested in him as a person, and to let him see who you have become. Even one honest story from a single question can be worth more than an hour of small talk.