80+ Questions That Can Unmask Someone’s Deepest Insecurities And Thoughts

Questions That Can Unmask

59. What’s the one harmful habit you have, that makes you feel amazing and free?

60. Have you ever cheated on someone?

61. How far have you gone to stay in the good books of someone?

62. Are you afraid of failure, or have you made your peace with it?

63. Are there any incidents in your childhood that still make you feel traumatized and scared?

64. Do you ever experience the fear that you might never be happy?

65. If your death was in your hands, how would you prefer to die?

66. Are you scared of dying alone?

67. Do you compromise on your values just to make someone else feel happy and secure?

68. What’s the biggest risk you have taken in your life, to date?

69. What is your deepest, darkest secret, that nobody knows about, not even your spouse?

70. What’s the strangest thing that annoys you?

71. What’s the strangest thing that makes you happy?

72. What is an absolute deal-breaker for you, when it comes to love and relationships?

73. What do you think you should focus more on, according to your loved ones?

74. What do you think you should focus less on, according to your loved ones?

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75. Do you ever find yourself pleasing someone who made YOU feel angry and humiliated?

76. What does it take for you to shut yourself down completely?

77. How frequently do you take responsibility for someone else’s bad behavior?

78. What are those 3 things that you absolutely want your future spouse to have?

79. What’s your ideal way of avoiding problematic people?

80. Have you ever abandoned yourself?

81. What is the one thing you crave to do because it makes you happy, but don’t do it, because you are scared that people might judge you?

82. Do you believe you can love two people at the same time?

83. What is your greatest fear?

84. If you were a superhero, what are the three things you would change in this world, first and foremost?

85. What do you think about when you are alone?

These questions are heavy and thought-provoking aren’t they? These questions might seem intimidating, but honest and truthful answers to them can really help you know and understand a person very deeply, including yourself. Try these out and see how you feel, and let us know your thoughts and experience in the comments down below!


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