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10 Great Questions to Ask Your Dad on Father’s Day

by | Jun 14, 2021

With Father’s Day coming up, I, like so many others, have been thinking about my dad who’s no longer with us and all the questions I’d like to ask my dad if I was still able to. Like most kids of my baby boomer generation, I really didn’t “know” the man I called Dad. I knew much of his story about what he had done in life, and there was no doubt about the values he had. But I didn’t comprehend how his life’s experiences had shaped him.

At nearly 95 years old, my mother is vibrant and healthy, and I am beyond grateful to have had her love and guidance as my parent. I’ve also seen her flourish as a grandmother and great-grandmother.

After this past Mother’s Day when we used the Raising Families Conversations with Mom guide to ask my mom about her own mother, grandmother, and personal experience being a mom, I learned so much about her and my family that I never thought to ask. We had such a nice conversation that it sparked my interest in all the things I never got to ask my father.

I knew that he was Native American and his own father never wanted to be associated with the tribe. Dad was a Marine at the battle of the Chosin Reservoir during the Korean conflict, where Marines had nearly 18,000 casualties with over 7,000 from the cold weather.

He was a police officer stationed in Watts, California, at the time of the first riots in 1965. He was a proud man, a serial entrepreneur, and one who didn’t know the meaning of “that’s not possible.”

He was also the man who taught me my work ethic. When I turned 7, I started working for him on the new home he was building for our family. I nailed down 1×6 boards to the floor joists. It wasn’t very exciting, but the thought of making 25 cents an hour was appealing to a 7-year-old.

I continued to work part-time for Dad until I was 21. In that time, I learned what it means to work, learned a ton of skills, and saw Dad lead a business and create value for his customers. During that whole time, I was never actually paid, though. It wasn’t until I turned 18 that I got my paycheck, in the form of a new 1970 VW Bug.

I knew how he handled business and what he expected of his workers. I knew his history in terms of the things he did, but there was so much I didn’t know about why he handled things that way or why he made the choices he did. To learn these things now would be a gift.

He passed eight years ago, so the opportunity to ask him some insightful questions is gone. I have memorabilia and my mother’s memories, of course, and those I cherish.

With my own children and grandchildren I have tried to be far more open and approachable about my past and my motivations as a father.

Hopefully, you still have the opportunity to talk to your father or grandfather or father-in-law this Father’s Day.

If your father is past the point of (or was never interested in) golf clubs or fishing gear, don’t miss out on your chance to receive this gift of knowledge and give your father the gift of a heartfelt conversation.

Use the list below to ask your dad (or others) some thought-provoking questions. No doubt there will be a few surprises in their answers.

10 Questions to Ask Your Dad for Father’s Day

  1. When you were a teenager, what got you into trouble?

  2. What’s the worst job you ever had?

  3. Of all the things your parents taught you, what do you think helped you the most?

  4. Do we have any famous or infamous people in our family tree?

  5. How did Grandma and Grandpa meet?

  6. What is your favorite memory of your parents or grandparents?

  7. What family traditions have you let lapse that you would like to bring back?

  8. Did you always want to become a father?

  9. What have you found most rewarding and most challenging about being a parent?

  10. How did you balance work and family life when I was young?


25 Questions to Ask Dad

    • Perfect for a memorable Father’s Day, birthdays, or other celebrations with parents of adult children
    • Record your conversation for an incredible family heirloom
    • Most questions adaptable for in-laws or grandparents
questions to ask your dad workbook

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Rick Stephens

Rick Stephens is a co-founder of Raising Families. With 33 years of experience as a top-level executive at The Boeing Company and having raised four children of his own, he is able to support parents and grandparents by incorporating his knowledge of business, leadership, and complex systems into the family setting. In his “free time” Rick enjoys road biking, scuba diving, visiting his grandkids, and generally trying to figure out which time zone he’s in this week. Read full bio >>