26 Questions To Ask Your Son Instead Of 'How Was Your Day?'

Connection is key to keeping boys close as they grow up.

Mom and son embracing, ready to talk, in front of a dark sunset Best smile studio via Shutterstock | Sedulur Grafis & Helga Frode via Canva

Watching our kids grow is so bittersweet. We get to watch our beautiful little babies become thoughtful, funny, unique human beings. At the same time, we know that our time with these little tiny boys will be short. 

In just a few short years, your sweet little boy becomes a gangly teenager who grunts out single-word answers from behind a hoodie and AirPods. He will be told to 'man up' and be tough, but he'll still need a place to be tender and vulnerable. 


If you want more than one-word answers, you need to know which questions to ask your son to help him feel like he always has a safe place to land.  

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26 questions to ask your son instead of 'How was your day?' to really get him talking

1. If you could make one law for the rest of your family what would it be?

2. What is your favorite thing about me?

3. What are three things I say a lot?

4. What is something you’ve learned from me?

5. What specific emotion or feeling do you try to hide from me?

6. What can I do right now to make your life happier?

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7. Do you think we would be friends if we were the same age?

8. What makes you awesome?

9. When was the last time you cried?

10. What do you love most about your life?

11. What is the last thing that I did that upset you?

12. What is your favorite thing to do when it’s just the two of us?

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13. What are some things I worry about that aren’t that deep?

14. What are the best and worst parts about getting older?

15. What is something you wish I would do more often?

16. If you won a million dollars what would you buy?

17. When was the last time I apologized to you and made you feel better?

18. What is the one thing you would do if you weren’t afraid?

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19. What about me do you hope never changes?

20. If you could switch places with me for a day, what would you do?

21. What do you need me to do when you are sad?

22. If you could change one thing about your life, what would it be?

23. When you describe me to your friends what do you say?

24. What is something that matters to you but no one else in our family understands?

25. What don’t I understand about what it’s like to be you?

26. Are you proud of me? Why or why not?

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This list was designed by the team at Open Relationships: Transforming Together, a podcast where people get real about making all the relationships in their lives better by inspiring meaningful conversations. 

Conversations don't have to be long or drawn out to build a strong connection with our boys. The goal is to prove to your son, time and again, that you are a fun, safe, and loving person to talk with. When he needs someone to turn to, he'll think of you. And that's the best gift you can give him and — yourself. 

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Joanna Schroeder is a parenting writer, editor, and media critic with bylines in The New York Times, The Boston Globe, Esquire and more. Her forthcoming book Talk To Your Boys: 20 Crucial Conversations To Have With Your Tween & Teenage Sons will be available in 2025 via Workman Publishing. More work is available via her Substack