50 Messed Up Questions That Will Either Strengthen Your Relationship Or Ruin It

1. Is there someone in your life that you wish were dead?

2. Have you ever gone to work while drunk?

3. Have you ever punched a wall?

4. Do you believe in the death penalty?

5. Have you ever spent the night in jail?

6. Have you ever driven while you were drunk?

7. What’s the weirdest thing you’ve ever masturbated to?

8. Have you ever bullied someone?

9. Do you own any firearms?

10. What was the biggest lie you’ve ever told?

11. Have you ever contemplated suicide — even for a second?

12. Do you believe in a heaven or a hell?

13. Did you drink before you reached the legal age?

14. Do you suffer from depression?

15. What about anxiety?

16. What’s the hardest drug you’ve ever done?

17. Did your parents ever hit you?

18. Have you ever intentionally hurt yourself?

19. Are there any alcoholics in your family?

20. Has anyone ever died in front of you?

21. What’s the meanest joke that you find funny?

22. Do you know anyone that’s committed suicide?

23. Do you think there’s a purpose to life?

24. How do you feel about atheism?

25. Have you ever stolen money?

26. Have you ever cursed out your parents?

27. How many funerals have you been to?

28. What are your thoughts on abortion?

29. Have you ever forced yourself to throw up?

30. What’s the most disturbing urge you’ve ever had?

31. Have you ever tortured an animal?

32. Have you ever broken into a place you shouldn’t have been?

33. Have you ever been high?

34. What’s the meanest thing you’ve ever done to another person?

35. Have you ever beaten someone up?

36. Have you ever been pulled over by a cop?

37. Have you ever told someone you loved them, even though it was a lie?

38. Have you ever been involved in a protest?

39. Would you ever spank your children?

40. Have you ever made fun of anyone over their weight?

41. Have you ever gotten blackout drunk?

42. Are there any curse words you refuse to use?

43. Have you ever smoked a cigarette?

44. Have you ever used someone for sex?

45. Have you ever given the finger to a stranger?

46. Have you ever blackmailed someone?

47. Are you friends with any drug dealers?

48. Have you ever liked anyone underage?

49. Have you ever cheated on a test?

50. Have you ever killed anyone? Thought Catalog Logo Mark 


About the author

Holly Riordan

Holly is the author of Severe(d): A Creepy Poetry Collection.