50 Revealing Questions To Ask Your Person To See If You Can Really Trust Them

A girl who trusts a boy
Unsplash / Annette Sousa

1. What’s the biggest lie you have ever told someone you were dating?

2. Have you ever said, “I love you” even though you did not mean it?

3. Do you kiss and tell? 

4. Do you have a guilty conscience after lying or sleep soundly at night? 

5. What is the closest you have ever come to cheating on someone you have dated in the past? 

6. How often do you lie to your friends to get out of hanging out with them?

7. Do you consider emotional cheating just as bad as sleeping with someone else?

8. When you start dating someone new, how long does it take you to delete your dating apps? 

9. Would you want your children to date someone like you?

10. Do you exaggerate when you tell stories to make them sound more interesting? 

11. Have you ever lied to get laid? 

12. When was the last time you were caught in a lie? 

13. What was the last promise you made that you ended up breaking? 

14. Would you rather give the hurtful truth or tell a little white lie? 

15. Have you ever blabbed about something you promised you would keep a secret? 

16. Do you trust your own judgement? 

17. What is the worst thing you have ever done? 

18. Have you ever lied to your boss to get an extra day off? 

19. Do you think most people are liars or genuinly good people? 

20. Have you ever gotten revenge on someone? How? 

21. Have you ever celebrated someone else’s failure? 

22. Do you gossip with your friends? 

23. Do you consider yourself a man (or woman) of your word? 

24. What would you do if you found out your best friend was getting cheated on?

25. What would you do if you found out your best friend was the one cheating on their partner? 

26. Would you agree to take a lie detector test?

27. Is there anyone you care about more than yourself?

28. Do you listen when others speak or plan out what you are going to say while they’re talking?

29. What is the meanest thing you have ever said to someone’s face?

30. What is the meanest thing you have ever said behind someone’s back?

31. Do you believe in second chances?

32. When was the last time you gave someone a genuine apology?

33. Are you okay with taking responsibility for your mistakes or do you always find someone else to blame?

34When do you think it’s okay to bend the truth? 

35. Are there any secrets you’re currently keeping from your parents?

36. Are there any secrets you’re currently keeping from your best friends?

37. Do you think it’s okay to keep certain secrets from the person you’re dating or do you tell them absolutely everything? 

38. What is your opinion on cheaters?

39. Have you ever stolen from your parents?

40. Have you ever stolen from your workplace? 

41. What’s the most manipulative thing you have ever done? 

42. Do you consider yourself a reliable person? 

43. Back in school, have you ever cheated on a test? 

44. Do you think it’s possible for couples to be 100% honest with each other? 

45. Have you ever lied on a job application? 

46. Could you date someone who has a history of lying to you? 

47. If you found a wallet on the ground, would you keep it or return it? 

48. What would you do if you realized someone was lying to you? 

49. Have you ever cheated in a previous relationship

50. Overall, do you consider yourself a good person? Thought Catalog Logo Mark

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