80 Questions To Ask Your Son To Get To Know Him

When I brought home my new baby, the worries immediately started.  No, scratch that.  

The worries started before my son was even born.  Was he going to be healthy?  What kind of person would he be?  

What would his favorite subject be in school?  Would he be one of the self-sufficient kids or would he just be interested in screen time and succumb to social pressure from older kids?   

The list continues on into infinity!  

However, the question that gave me a hard time in my mind and still is on most days is this:  Am I going to be a good parent? 

I thought about all the things I was prepared for.  I thought I knew about most of the everyday chores such as changing diapers, feeding my child and generally keeping him alive to the best of my ability.  

Then I let my mind wander into the dangerous territory of what happens when he becomes a teenager (cue ominous music in the background!)  

After a few very sleepless nights, I came to the realization that the only control I really had over his teenage years and how we would interact with each other is by starting a good relationship early in his life, thereby building a connection that would be solid enough to usher us safely through the teenage years.  

Armed with this concept, I eagerly launched myself into this new idea.  The first thing I needed was the right questions that would lead to meaningful conversations with more than one-word answers.  

What I learned was pretty eye opening, at least to me.  People are complicated.  

Young children are insightful and will see through the best laid plans you have to get to know them.  

I am a pretty straightforward person, so I marched myself right to my son and started asking all sorts of  simple questions and funny questions, even silly questions.  Long story short, I was full of great questions!  

Or so I thought.  

My son was not ready for the onslaught of what I thought were fun questions.  

At all.  

I was not ready for his response.  My amazing, expressive child looked at me, hid under the dining room table, and said “No Mom, I don’t want to talk about that!”  

This to me felt like the worst thing ever.  I had a perfect day in mind where I would ask him a lot of questions and spend quality time, thereby solidifying a strong relationship that would help us skate through the high school years.  

Nope. That didn’t happen.  

I went back to the drawing board.  I had a good idea but didn’t execute it correctly. 

This article will not only arm you with some of the best questions to ask your son, but also help you understand how and when to ask these questions.   

If you are in the same boat as I was, I would direct you first to the following list of questions for kids like would you rather questions, this or that questions and if you have a daughter, questions to ask your daughter.  

So join me and we will dig into these questions to get you started on the best part of a journey to get to know your son! 

And if you have a daughter, use these daughter questions to have fun question/answer session.

Types of Questions to ask your son:

1.Questions that allow him to teach you

2.Questions that help him build emotional intelligence

3. Would you rather questions

4. Silly questions

5. Self-esteem boosting questions

6. Thought-provoking questions

7. Questions about family and friends

Before I set you up with a more detailed list of these questions, let’s talk about when and how to ask them.  What is just as important as the question itself is your approach and how much you are willing and able to be in the moment with your son.  

In addition to that, you may want to make sure that your son is ready to interact with you.  

Do not try to start a meaningful conversation while he is focused on a solo project like playing a video game.  Instead, go for a walk or start a project together that you both enjoy and let the conversation flow naturally. 

Some of my favorite conversation starters are funny, open ended questions that can lead to a longer conversation.  

Understand that sometimes he will just answer your one question and be done and that is okay.  

Even one question can make all the difference and show your son that you care about him and what he thinks.   

Questions To Ask Your Son

Questions That Allow Him To Teach You

1. How do you play your favorite sport?

2. How did your favorite superhero get his/her powers?

3. Teach me about your favorite activity.

4. Teach me your favorite dance moves.

5. Teach me the words to your favorite song.

6. Tell me about how you learned your favorite bike tricks.

7. Tell me the characteristics of your favorite cartoon character.

8. Tell me the story of your favorite tv show and why you like it.

9. Tell me about your favorite toy collections and what you like about them.

10. Teach me how to play one of your video games.

11. Tell me about your favorite book.

12. Teach me how to make your favorite food.

Questions That Build Emotional Intelligence

13. What brings you joy?

14. What is your favorite joke?

15. What makes you laugh?

16. How do you feel after a long school day?

17. What is it that you like about your favorite teacher?

18. What is your favorite part of the school day?

19. What is your least favorite part of the school day?

20. What kind of animals make you feel happy?

21. What kind of animals make you feel scared?

22. Tell me about the funniest person you have met.

23. Tell me about what characteristics make a good friend in your mind.

24. What is the hardest thing you have done in your life?

25. What is your favorite family tradition?

Would You Rather Questions

Would you rather questions can be a good ice breaker before asking more serious questions.

Especially these gross would you rather questions because they are hilarious!

25. Would you rather have the ability to fly or teleport?

26. Would you rather have a time machine or live in a different time period forever?

27. Would you rather never have to brush your teeth again or never have to shower again?

28. Would you rather eat a dead bug or a live worm?

29. Would you rather live in a city or a desert island?

30. Would you rather go to the doctor or the dentist?

31. Would you rather be a wizard or a superhero?

32. Would you rather live among the clouds or at the bottom of the ocean?

33. Would you rather be super strong or super fast?

34. Would you rather be able to talk to animals or read people’s minds?

35. Would you rather have a lion head or a lion tail?

Silly Questions

36. What is the grossest thing you can imagine?

37. If you were part of a circus act, what would your job be?

38. If you could be any animal, what would you be?

39. If you could be invisible for one day only, what would you do?

40. If you could visit one planet in the universe, which one would it be?

41. If you could have superpowers, which ones would you have?

42. If you had three wishes, what would they be?

43. Tell me about the funniest thing you have ever seen.

44. What would you do if you were in charge at school today?

Some silly this or that questions could be fun too!

Self-Esteem Boosting Questions

Boosting a boy’s confidence is so important, but is often overlooked.

45. What are you good at?

46. What do you like about yourself?

47. What words would you use to describe yourself?

48. Do you prefer a lot of friends or a few really good friends?

49. What makes you unique?

50. What makes you feel like you are on top of the world?

51. How do you feel when you have helped someone?

52. What is one of the best ways to make you feel better when you are sad?

53. What do you do when people treat you unkindly?

54. What makes you feel proud of yourself?

Thought-Provoking Questions

55. If you could change anything about your life, what would it be?

56. What is your biggest fear?

57. What are you thankful for?

58. Tell me about your best friend.

59. How do you overcome your weaknesses?

60. Tell me about your favorite place in the world?

61. What is your happiest memory?

62. What makes you sad?

63. What can we do to be better parents for you?

64. What do you want to do for the rest of your life?

65. If you could change any rule, which one would it be?

Questions About Family And Friends

66. What do you like/dislike about being an only child?

67. What do you like/dislike about having siblings?

68. If you could change anything about your family, what would you choose?

69. If you could change any family rules, what would they be?

70. What do you have in common with family members?

71. How are you different from your family members?

72. Who would you like to spend more time with?

73. What kinds of thing would you like to talk about at the dinner table?

74. What is your favorite thing about your family?

75. What can we do to be better parents?

76. What is the most important thing to you about your family?

77. What is the best thing in your life?

78. What is the worst thing in your life?

79. What are you excited about in your life?

80. What would you do if you made the rules at home?

81. What is your favorite family activity?

You have some questions, now what?  Make a plan (sort of!)

1. Hold on to this post for question inspiration.  

2. Put the phone away!  Lock it up.  Put it in time out.  Give your son your full, undivided attention.

3. Be casual.  Ask a question during a walk or while you are completing a task together such as cooking, repairing an item or working on a project together.

4.  Let your son lead the conversation.  Resist the urge to lecture.

5.  Remember that this is building a relationship with your son, not another thing on your to do list!  Relax and enjoy your child and this precious time you have with him.