23 Insightful Questions to Ask Your Dad

Updated February 23, 2021
Father and happy daughter strolling on the beach

Getting to know your dad on a deeper level is sometimes just a few select questions away. Once you decide what the best questions to ask your dad are, it can lead to incredibly meaningful conversations between you two.

Questions to Ask Your Dad

Regardless of the relationship you had or have with your dad, you may find yourself curious about his life and his decision making. Asking your dad questions that wouldn't come up on a day-to-day basis can help you better understand his inner workings.

1. When It Comes to Raising a Child, What's the Best Advice You've Ever Received and How Did You Apply That to Raising Me?

This question can give you a peek into what your dad was like when he was just starting off as a father. Whether you are a parent yourself now, plan on becoming a parent one day, or are just curious about your father's parenting style, this question can lead to an insightful chat about raising a child.

2. What's One Piece of Practical Advice You Wish You Knew Sooner?

Passing down wisdom learned from past experiences can not only potentially help you in your life, but can give you a better understanding of what your father values as solid advice.

3. What Is the Worst Advice You Ever Took and How Did That Play Out?

This question may lead to a funny conversation or a highly emotional one, depending on what the circumstances around the advice were. Either way, you'll get a glimpse into your dad's thought process and how he reconciled taking said bad advice.

Father and son talking while sitting in living room

4. What Relationship Tips Do You Think Have Helped Keep Your Friendships and Romantic Relationships Strong?

This question can help you understand what your dad values when it comes to relationships and what he thinks keeps them solid. While you may or may not agree with his relationship advice, it may still be interesting to hear his perspective.

5. When Did You Know You Were Ready to Be a Father?

Asking this question can help you conceptualize your dad's mind frame around becoming a parent.

6. Can You Tell Me About the First Moment You Felt Like a Good Dad?

This can lead to a sweet story about your dad's idea of what being a good father means to him, as well as a special memory shared between you two that you may not recall.

7. What Do You Do When You Regret a Decision You've Made?

It can be interesting to learn about how others, especially parents or caregivers, deal with difficult emotions and challenging decisions. This questions can give you some insight into your dad's experience with regret.

8. How Do You Handle Feeling Overwhelmed?

Everyone feels overwhelmed at some point in time. Hearing how your dad handles this feeling can not only be interesting, but lead to practical advice about feeling overwhelmed.

Deep Questions to Ask Dad

If you want to dive deeper and ask more emotionally charged questions, be sure you both are in the right mind frame. You may ask your dad ahead of time if he's up for discussing more difficult or emotionally intense topics with you, instead of asking these questions without permission.

9. What Single Experience Has Significantly Shifted Your Perception of Yourself and Why?

This may be a question your father hasn't ever thought about or discussed with anyone. It can be fascinating to see if he can quickly pinpoint a situation that has changed his view of himself.

10. How Have You Grown and Changed as a Person and What Has Had the Most Significant Influence on Why?

Asking self reflecting questions can give you great insight into the person your father has developed into.

11. Was There Ever a Moment With Me Where You Wished You Reacted Differently and How So?

This question can be interesting to ask your dad and may lead to a surprising answer that allows you two to connect on a deeper level.

12. What Do You Tend to Do When Situations Feel Stressful, and Who Do You Think You Learned This From?

This question can help you understand your dad's relationship with stress and may uncover some family coping patterns that may or may not impact you as well.

13. If You Could Go Back in Time and Change Any Single Decision, Would You? Why or Why Not?

You may hear a story you've never heard before, while also getting a glimpse into your dad's relationships with regret, self-doubt, and decision making.

14. What Memory of Your Parent(s) Tends to Bring up a Lot of Emotion for You?

Whether you've heard a lot about your grandparents or not, it can be interesting to hear what experiences most resonated with your dad when it comes to his parent(s).

15. What's One Memory That Tends to Come Up Often for You?

Many people experience one or multiple memories that tend to pop up often. It can be very telling to hear about which one feels most poignant to your father.

16. What's Something You Wish You Told Your Parent(s) But Never Did?

While this question can bring up difficult emotions, it can be fascinating to hear your dad's response as it can give you a glimpse into his relationship with his parent(s).

17. Was There Ever a Moment Where You Felt Like You Were Acting Liking Your Parent(s)?

Asking this question can offer you some insight into family patterns within your family system. You can also self reflect to see if you've perpetuated these family patterns as well.

18. What's One Thing You Always Wanted to Tell Me but Didn't?

This question can lead to many types of answers, but either way, it's a good opportunity for your dad to be honest with you and share something he hasn't before.

Funny Questions to Ask Your Father

Funny and lighthearted questions are a great way to better get to know your dad and understand his sense of humor.

19. Can You Tell Me About a Time You Pulled an Epic Prank?

Even if you know your dad as more serious now, it doesn't mean he never pulled a prank. You may be surprised by his answer to this question.

20. What's Your Favorite Dad Joke?

Your dad may have a favorite joke that he just can't get enough of. If you don't already know it, you can ask him to see what it is.

Happy father with adult daughter on the beach

21. What's the Most Rebellious Thing You Did Growing Up and Did You Get Caught?

Even if your dad doesn't seem like the rebellious type, he may have made some choices that you find surprising and entertaining.

22. What's the Most Stubborn Teenage Moment You Remember?

Teenagers can definitely have a stubborn tendency. Find out more about what your dad was like as a teen by asking this question.

23. What or Who Do You Remember Making You Laugh as a Child, Teenager, and Young Adult?

It can be interesting to hear about what your dad finds particularly funny and how his humor has changed throughout the years.

What Questions Should I Ask My Dad?

When it comes to asking your dad questions, think about what you want to know and why. You can ask:

What Questions Should I Ask My Dying Father?

If your father is in the process of passing away, you may find yourself compelled to get to know his history a bit better. Create a list of questions that you feel are important to know and record or write his answers down so you can keep his unique experiences within the family forever.

Questions to Ask Your Father

Asking your father meaningful questions is a great way to better understand him and his unique history.

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23 Insightful Questions to Ask Your Dad