111 Loaded Questions That Reveal Someone’s Biggest Insecurities, Vulnerabilities And Emotional Baggage

A loaded question is one that is ripe with assumption and the ability to unravel someone’s deepest desires, vulnerabilities and emotional baggage. It is a question that implies something about its listener; it presumes to know some aspect of that person’s being, personality, and preferences. These questions disrupt the listener’s usual ways of thinking and simultaneously uncover their true self. Due to its hidden implications, the person who asks the loaded question gains control over the dialogue and the person being asked caters their answer to only the context of the question.

You can ask yourself these loaded questions to better understand yourself, or you can pose these questions to others to better understand them. Whether you’re dating someone new, building a new friendship or forging a business partnership, a loaded question can be an insightful way to discover the truth. However, it should be done in a time-appropriate and context-appropriate manner. One should not ask a loaded question without considering the other person’s sense of comfort or the nature of the relationship; normally these should be asked once you’ve already achieved a level of rapport, otherwise, you’re just shooting blanks.

When asking loaded questions, always respect the boundaries of others. You must also be okay with the other person refusing to answer the question – sometimes their refusal will speak more volumes than their answer ever would, anyhow. Always be aware that a person may or may not answer honestly. In fact, some of these are so revealing that it’s very possible they won’t! Yet you can find out a lot about a person even just by the way they choose to respond.

Here are 111 loaded questions you’ll want to ask that can help you reveal someone’s true self:

1. What’s your favorite strategy for avoiding tough situations?

2. How often do you do things just for the attention?

3. Would you prefer to be manipulated or to be the manipulator?

4. What did your previous partners always tell you to do more of?

5. What did your previous partners always tell you to do less of?

6. Who do you look to blame when things go wrong?

7. What is the one thing people assume about you that you wish was true?

8. What is the one thing people assume about you that you wish wasn’t true?

9. When was the last time you lied to protect your image?

10. How often do you put on a happy face when you’re really not feeling it?

11. When do you think you began putting your guard up so much?

12. Who made you feel most anxious when you were a kid?

13. How do you speak about others when they’re not around?

14. What aspect of your life are you most delusional about?

15. How often do you admit you were wrong?

16. Which one of your biggest flaws do you like to rationalize the most?

17. Is it your fear of commitment or your fear of intimacy that makes you shut down more?

18. At what stage of a relationship are you most likely to withdraw emotionally?

19. What is the one compliment you always get that you’re too embarrassed to accept, so you deflect it?

20. What would your ex say is your worst habit?

21. What is the one insecurity you’re pretty sure has some basis in reality?

22. When was the last time you felt really insecure about the parts of yourself you pretend don’t exist?

23. What is the most interesting white lie you’ve told?

24. Do you ever feel like an imposter?

25. Do your friends know how competitive you are?

26. What’s the worst part about being in a relationship?

27. What’s the hardest part about dating nowadays?

28. What’s the hardest thing about being rejected?

29. How do you deal when you know you’re being irrationally jealous?

30. How do you deal when you know someone’s not willing to give you what you want?

31. What’s the weirdest thing you’ve ever wanted someone to do to you in bed?

32. Are you ever afraid of people knowing who you really are?

33. If you went to a therapist today, what would they say is holding you back the most?

34. When was the last time you lowered your standards just to get someone else’s approval?

35. What do you like most about being a flirt?

36. Is it fun using your sexuality to get what you want?

37. Is your need for revenge greater than your need for peace?

38. Have you stopped trying to control things yet?

39. Which parts of yourself do you still seek validation for?

40. How do you cope with being unfairly ignored?

41. Do you like punishing yourself for things that are out of your control?

42. What did your co-workers say was your biggest problem when communicating?

43. Are you okay with not knowing what happens next?

44. Will you ever feel okay with being imperfect?

45. Does sabotaging yourself give you an odd sense of comfort?

46. How do you feel about being disliked by some people?

47. Are you afraid of missing out on love because you were always looking for the next best thing?

48. What’s the strangest thing you’ve done just to avoid failure?

49. What is the biggest risk you’ve taken just to prove yourself?

50. What’s the boldest thing you do every day, just to feel like you’re still in control?

51. What accusation would you defend yourself most fiercely against, even though you know it’s true?

52. What’s the most toxic thing about yourself you actually kind of secretly like?

53. How much do you enjoy being in control?

54. When do you give yourself permission to lose control?

55. What guilty pleasure are you currently justifying to yourself?

56. What is the most passive-aggressive way you’ve dealt with your rage?

57. What is the pettiest and most immature way you’ve avoided losing face?

58. What’s the worst habit you have that rewards you the most?

59. How do you get your needs met when you’re alone?

60. Are you more emotionally stable when you’re single or in a relationship?

61. What is the most ridiculous thing you’ve done to please people?

62. What is the most ridiculous way you’ve rebelled?

63. What’s your favorite way to channel your aggression?

64. What’s the most shallow trait in a person you’re willing to give up your standards for when you’re dating someone?

65. How do you cope with being betrayed?

66. How quickly do you get over an ex, even if you remain friends with them?

67. Are you okay with disliking someone?

68. What is your favorite form of self-destruction?

69. What’s the one thing you struggle most to manifest in your life?

70. What’s the one thing that you manifest so easily, people are jealous of it?

71. What’s the most irrational reason you’ve ever had for disliking someone?

72. What’s the most taboo fantasy you’ve ever had?

73. What is one fear that you’d be ashamed of your friends knowing about?

74. Which one of your deepest secrets do you think is the least common?

75. What’s the most irrational reason you’ve liked someone?

76. How do people normally know you have a crush on them?

77. How do people normally find out you hate them?

78. What is your go-to strategy to deflect criticism, even constructive criticism?

79. How do you divert from someone calling you out on something you’re afraid to own?

80. What is one thing you’re afraid to own about yourself that others have already pointed out to you?

81. What is one thing people always get wrong about you?

82. What emotion motivates you the most when you’re down?

83. What emotion makes you want to give up?

84. Are people shocked when you stand up for yourself?

85. How often do you say yes to the things you really want to say yes to?

86. How often do you say no to the things that make your skin crawl?

87. What shallow aspects of a person do you focus on even at the expense of seeing their true self?

88. How far are you willing to go to maintain a relationship, even an unhealthy one?

89. What is the one thing you always do not because you like it but because you want someone’s approval?

90. What would be the one thing you’d be willing to give up just to be loved?

91. What is the worst way someone’s ever abandoned you?

92. What is the worst way you’ve ever abandoned yourself?

93. How do you entertain yourself when you’re not around people?

94. Are you happier alone because you enjoy being alone or because you prefer it to being surrounded by horrible people?

95. What is the one trait you look for that tells you this person is compatible with you?

96. What habit do you know you could quit but don’t want to?

97. What is your favorite strategy for avoiding difficult people?

98. What is your favorite strategy for avoiding conflict?

99. What is the weirdest thing that gets you angry?

100. What is the weirdest thing that makes you sad?

101. What do you love most about your sexuality?

102. What do you hate most about your sexuality?

103. What part of your sexuality do you repress the most?

104. How often do you take responsibility for other people’s crappy behavior?

105. When are you most likely to shut people out?

106. Which insecurity would shock people if they knew about it?

107. What do you find yourself justifying to people, even when no justification is needed?

108. When was the last time you tried to please someone who made you angry?

109. What do people often tell you need to focus more on?

110. What do people often tell you need to focus less on?

111. What is the one thing that could make you happy, but you refuse to do it because you’re afraid of what others would think?