42 Deep Questions to Ask Your Dad

As we get older, we realize we don't always know our dads as well as we'd like to. So, we’ve put together meaningful questions to help you get to know your dad better and maybe even spark some great conversations.

And if your dad is getting older, our book is a cool way to keep his stories alive for years to come. 

1. Looking back on your career, talk about something you regret.
2. How old were you when you became a dad?
3. What did you want to be when you were a child?
4. Describe your first pet.
5. How do you define success?
6. What was the most important lesson you learned about managing your own finances?
7. How far back do you know your family history?
8. Talk about a time in your career when you hurt someone to get ahead.
9. How has your relationship with your siblings changed over time?
10. Looking back at your career, what do you feel you accomplished?
11. Talk about how your career affected your role as a father.
12. Talk about the kind of child you were.
13. Talk about the hardest struggle you experienced as a child.
14. Talk about whether family history and heritage are important to you.
15. What was the most surprising part of becoming a dad?
16. Looking back on your career, talk about something you loved doing.
17. Talk about a mentor who helped you along the way.
18. Talk about a moment in your career that you felt like giving up.
19. Tell a story about one of your siblings.
20. If you had one thing to say to your children what would it be?
21. How did becoming a father change you?
22. What is your earliest memory?
23. Were you are you a good father?
24. What were the low points of being a father?
25. How did becoming a father challenge you?
26. Tell the big family myths about your ancestors!
27. Was your career a life's calling or just a way to make money?
28. What were the high points of being a father?
29. Talk about a moment you made a major change in your career.
30. Talk about whether you had a large or small extended family.
31. What is the funniest pet story you have?
32. Tell the story of meeting the love of your life.
33. How did you know they were the one?
34. What were your ambitions when you began your career?
35. What do you love about your pet/s?
36. Talk about the craziest thing you did after 40!
37. If you could change one thing about your fatherhood what would it be?
38. What were your favorite games growing up?
39. What is the funniest story you have about being a father?
40. Describe your happiest childhood memory.
41. Describe a special moment from your childhood.
42. Talk about your personal values.

Engaging your father with thoughtful questions can be a transformative experience for both of you. These conversations offer a unique opportunity to deepen your relationship, gain valuable insights, and understand the man behind the role of 'Dad.' By exploring his life experiences, values, and perspectives, you may discover facets of his personality you never knew existed. Remember, the goal isn't to interrogate, but to create an open dialogue where both of you feel comfortable sharing. Be prepared for answers that might surprise you, challenge your perceptions, or even inspire you. This exchange isn't just about learning your father's story; it's about strengthening your bond and creating new shared memories. So, whether you're catching up over a shared hobby, during a long drive, or simply over a cup of coffee, take the time to ask these questions. The understanding and connection you gain may well become one of the most valuable gifts in your relationship with your father.

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