50 Midnight Questions To Ask Your Person When You Just Don’t Want To Fall Asleep

1. What’s the wisest piece of advice your mother has ever given you?

2. What was the worst haircut that you’ve ever gotten?

3. If you died tomorrow, who do you think your death would impact the most?

4. What question do you not want me to ask you?

5. What was your favorite snack when you were a kid?

6. How did you come up with the name for your pet?

7. What is the worst physical pain that you’ve ever experienced?

8. What is the worst emotional pain that you’ve ever experienced?

9. What book was so bad that you didn’t even finish it?

10. Are there any colors that you refuse to wear?

11. What one thing are you most proud of accomplishing?

12. If you could be interviewed on any talk show, which one would it be?

13. What’s the scariest ghost story that you’ve ever been told?

14. Are there any dreams or nightmares that stick out from when you were a child?

15. What do you think is the worst crime a human could commit?

16. If you were reincarnated, would you want to be a boy or a girl in your next life?

17. What artist do you wish would be taken off the radio?

18. Have you ever witnessed something unexplainable?

19. If you could go back to high school, what would you do differently?

20. How long do you think you could last without having intercourse?

21. Are there any mythical creatures that you believe in?

22. Is there a specific teacher that made your life miserable?

23. What TV show or movie do you want to watch, but haven’t gotten around to it yet?

24. Do you think any of your coworkers deserve to be fired?

25. When you were little, what scenarios did your Barbies (or G.I. Joes) act out?

26. Do you like the color of your eyes?

27. Do you believe that animals experience emotions in the same way that humans do?

28. What’s the most embarrassing dare you’ve ever completed?

29. What common food have you never actually tried?

30. What’s your favorite cat breed?

31. What’s your favorite section of the newspaper?

32. Which 90s show do you wish they’d bring back?

33. Did your parents ever tell you why they chose your name?

34. What is one memory that you wish you could erase from your mind?

35. What TV show did you once love, but eventually gave up on watching, because it got that bad?

36. What (if anything) were you bullied over when you were little?

37. What’s your favorite font to use when you type?

38. What age were your parents when they had you?

39. What’s the most embarrassing video in your recent Youtube history?

40. Have you ever seen a person (or a dog or a cow) give birth?

41. Do you think you’re overpaid or underpaid?

42. Have you ever killed a houseplant?

43. Is there a specific number that holds a lot of meaning to you?

44. On average, how many times do you wake up in the middle of the night?

45. Do you know your IQ?

46. Do you know your Myers Briggs personality type?

47. Which Netflix show do you think is overrated?

48. What is your favorite month of the year?

49. Which family member do you secretly hate?

50. Has a celebrity ever replied to one of your Tweets?