I used to think knowing my kids was automatic. I made them! Of course I know them. But our kids change constantly, and the parts that change fastest are the parts we can’t see, their fears, their friendships, what they’re proud of, what they’re quietly worried about at eleven o’clock at night. If we’re only talking about homework and what’s for dinner, we can go months without noticing.

Here’s the thing, feeling known is not the same as feeling loved, and kids need both. A child can be certain you love them and still believe you don’t really get them. That gap is where the pulling-away starts.

So I started asking better questions.

75 Intentional Questions to Ask Your Child

Print these, screenshot them, keep them in your notes app. You don’t need to go in order – just pick whichever one you’re most curious about today.

Identity & Self-Awareness

1. What are three words that describe you right now?
2. What are your top three strengths?
3. What is your biggest insecurity at the moment?
4. What is your favorite quality about yourself?
5. What is your least favorite quality about yourself?
6. What makes you feel the most like yourself?
7. How do you hope people describe you?
8. What makes you feel misunderstood?
9. When do you feel the most confident?
10. Who are you becoming?

Emotional Intelligence

11. How do you like to be comforted when you’re upset?
12. What overwhelms you lately?
13. What do you do when you feel angry?
14. What are you most afraid of right now?
15. What helps you calm down fastest?
16. What makes you feel safe?
17. What makes you feel the most seen?
18. What do you dread doing — and why?
19. What’s something that never fails to make you feel better?
20. What emotion do you feel most often these days?

Relationships & Belonging

21. Who do you trust most? Why?
22. What do you value most in a friendship?
23. What makes someone a good leader?
24. What kind of friend do you want to be?
25. What do you want people to feel when they’re around you?
26. Who are you most similar to in our family?
27. What is your favorite part of our relationship?
28. When do you feel closest to me?
29. What makes you feel left out?
30. Who has influenced you the most this year?

Growth & Character

31. What was your proudest moment?
32. What is something you failed at but learned from?
33. What’s a mistake that taught you something important?
34. What do you wish you handled differently recently?
35. What makes you feel unstoppable?
36. What is something you want to improve about yourself?
37. What habit would make your life better?
38. What kind of person do you admire most?
39. What is the biggest compliment someone could give you?
40. What does integrity mean to you?

Dreams & Future

41. What is one dream you’ve never said out loud?
42. What are your biggest goals for this year?
43. In 10 years, how would you like to describe your life?
44. If you could try anything without fear of failure, what would you do?
45. What are you curious about right now?
46. What hobby have you always wanted to try?
47. If you had a free year to do anything, what would you choose?
48. What do you want your legacy to be?
49. Do you think you have a calling? What might it be?
50. What’s something you’ve delayed that you know you should start?

Gratitude & Perspective

51. What are five things you’re thankful for right now?
52. What do you love most about life?
53. What gives you hope?
54. What is something most people take for granted?
55. What family tradition means the most to you?
56. What advice has stuck with you?
57. What is something you enjoy now that you used to dislike?
58. If today was your best day, what would it include?
59. What makes an ordinary day feel special?
60. What is one small thing that brings you joy?

Reflection & Memory

61. What is your earliest memory?
62. Tell me about a day you’ll never forget.
63. What childhood moment shaped you most?
64. What was your favorite age so far? Why?
65. What’s your favorite memory of us?
66. What was the first thing you bought with your own money?
67. What’s something I did for you that mattered?
68. What is something you wish I understood better about you?
69. If you could give your younger self advice, what would it be?
70. What season of life has felt the hardest so far?

Fun & Imagination

71. If you could have dinner with anyone living or dead, who would it be?
72. If you could time travel, where would you go?
73. If there were 26 hours in a day, what would you do more of?
74. If you had three wishes right now, what would they be?
75. What would your ideal weekend look like?

If Questions Feel Awkward, Make It a Game

Some kids light up when you ask them something directly. Others need the pressure taken off completely, and that’s where a game does the work for you. Nobody has to be vulnerable on purpose – you’re just playing, and the real conversation sneaks in the side door.

Here’s my Amazon list of games with questions for kids if you want somewhere easy to start.

One Last Thing

You are not going to get through 75 questions. You might get through four, and two of them will get one-word answers, and that is still four more than you would have asked otherwise.

Start with number 10 – who are you becoming? – and just see what happens. I promise your kid is more interesting than you remember, and they have been waiting for someone to be curious about them.

Tell me in the comments which question surprised you the most. I want to know!