Ate Advice Blog Parenting

Convo-Provoking Hypotheticals to Ask Your 8 Year Old (& More!)

School is back in session! Our little guy starts in about a week, but I know many more kids have already taken the big steps towards their new school year (after taking a picture with a sign that includes their name, age, grade, and dream job of course!). I know we never have a problem having a conversation with our walking talkie, but I also know it’s difficult to really get a picture of what they’re experiencing at school.

It’s like a hill: you start at the bottom and, just because of age and language, the conversations are light and sometimes short. As they get older, they want to share every detail with you (over and over and over…). However, it’s typically about something that happened at the playground or a single moment they had with their friends. Then they get to the age where they no longer want to share their day with you.

How do we engage with our kids more?

My son and I love to play hypothetical gams (“If”, “Either/Or”, etc.). It’s a game to us both, plus it gives me insights on what he’s into and how he uses his brain.

To help you get started, here’s a list of convo-provoking hypotheticals, and questions and statements to get you started! BONUS: Plus some follow-ups to keep the conversation going!


1. If you could attend school as any book or movie character, what would it be?
2. If you were the teacher, what would you teach?
3. If you had special powers to help with schoolwork, what would they be?
4. If your school only taught two classes based on today, what would you pick?
5. If you could remodel the school, what would you change?
6. If you could switch teachers, who would you pick?
7. If you could only read one book for the rest of the year, what would it be?
8. If you could make up a school holiday, what would you celebrate?
9. If you could change the school mascot, what would it be?
10. If your mascot had special powers, what would they be?

Keep reading below, and/or Pin it for later!

Tell me about…

11. The funniest part of your day!
12. Something you were amazed by!
13. Your class pet!
14. An embarrassing moment.
15. One thing you learned today that you did not know yesterday.
16. A challenge you faced.
17. –How did you overcome it?
18. –What are other ways to overcome it?
19. A moment of kindness.
20. A moment of someone being unkind.
21. –How did you respond?
22. Your substitute teacher.
23. –What did she do differently from your teacher?
24. A moment of bravery for you (or a friend!)
25. Your favorite and least favorite part of today!
26. The drills you had today.
27. A moment you felt proud of yourself!
28. A moment where you helped a classmate!
29. An upcoming project.
30. Your favorite part of the school building.


31. What do you think you’ll learn this year?
32. What do you hope never happens again?
33. What do you hope does happen again?
34. Who did you sit with at lunch?
35. What was your favorite part of lunch?
36. What did you do during recess?
37. Was there anyone sitting on the Friendship Bench?
38. –Did you ask them to join you to play with?
39. Did you sit on the Friendship Bench?
40. –What happened when you sat there?
41. What did you find at the library or book fair that you’re interested in?
42. Did you meet anyone new today?
43. –How did you meet them?
44. –Do you think you’ll become good friends?
45. What are you reading in school?
46. Who got in trouble/timeout today?
47. What surprised you today?
48. Did you ever feel unsafe or scared?
49. What made you laugh today?
50. What made you upset today?

Share with me what you ask your kids after school, and some of the best responses you've received!

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