Connecting with teens and tweens can be challenging, and grown-ups (including well-meaning teachers) may find themselves firmly on the outside trying to look in. Looking for new ways to reach out? Here are 50 questions to ask middle and high school kids to check in and get to know them better. 

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1. What can I, as your teacher, do to help you this year?

2. What five words do you think most describe you?

3. What do you like best and least about school?

4. If you were famous, what would you want to be famous for?

5. Of all the things you are learning, what do you think will be the most useful?

6. Think about your favorite teacher you’ve had so far. What are the characteristics of this teacher that you like?

7. Where is your favorite place in the world?

8. If you could travel back in time three years, what advice would you give yourself?

9. If you could make one rule that everyone in the world had to follow, what rule would you make? Why?

10. What do you love and are passionate about?

11. What is your best quality or greatest strength?

12. Tell me something you want me to know about you.

13. How do you like to study?

14. What does your daily life look like? 

15. Would you like to attend college? If so, which colleges are your top three?

16. What career(s) would you like to pursue? List at least one career.

17. You discover a beautiful island where you decide to build a new society. What is the first rule you put in place?

18. Is there an app you hate, but you still use it anyway?

19. What’s the riskiest thing you’ve ever done because someone dared you?

20. What does creativity mean to you? Give an example of you being creative.

21. Would you change your name if you could? What do you choose and why?

22. What’s your first memory?

23. Who is most inspiring to you?

24. What would be one of the first things you would do if you became president?

25. What motivates you?

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

27. What are you most afraid of?

28. If you could be someone else for a day, who would you be and why?

29. What are three things that you do every day?

30. What is something you do that bothers other people?

31. Pick a word to describe your future. Why did you choose that word?

32. What is one thing that you like about yourself?

33. What superpower would you like to have and why?

34. Talk about a funny or scary adventure you had with a friend.

35. Are you organized or messy?

36. Talk about something happening in the world that concerns you.

37. Talk about something happening in the world today that inspires you.

38. If you could move anywhere, where would you live?

39. What do you know how to do that you can teach to others?

40. What five things would you take with you during an zombie apocalypse and why?

41. At what age is a person an adult? Why do you think so?

42. What is something about yourself you could totally brag about, but usually don’t?

43. You can either leave your hometown forever or never leave your hometown. Which do you choose?

44. What is an unwritten rule about school that everyone knows anyway?

45. Would you cheat on a test if you knew you would not get caught? Why or why not?

46. What’s your greatest accomplishment so far?

47. What do you do when you can’t sleep at night?

48. Have you passed up on any chances that you now regret? What were they?

49. Looking back at the end year, how would you describe a successful year? 

50. What advice would you give yourself to make this a better school year?

Plus check out Reaching the Students Who Don’t Have Reliable Internet Access

If these questions to ask middle and high school kids inspired you, join our WeAreTeachers HELPLINE group and come talk with the very teachers who suggested them!