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

Questions That Can Unmask

Everyone has insecurities, emotional baggage, and uncomfortable thoughts that they don’t readily share with others. Maybe because they fear being judged, or maybe they just don’t feel comfortable with being vulnerable in front of others. However, there are quite a few interesting questions that can bring out someone’s insecurities, deepest thoughts, and vulnerabilities to the forefront.

Now, asking these questions is not about forcing someone to talk about things they don’t feel comfortable talking about, nor is it about trying to pry about their personal business. The main motive of such questions is to know someone better on a more emotional and intimate level; you can even ask yourself these questions to understand yourself and your thoughts on a much deeper level.

If you are building up a new friendship with someone, or embarking on a new relationship, trying to know them on a more personal and deeper level is always a good idea, isn’t it? Having some insight into the person and their perspectives will help you get to know them better. However, before asking any of these questions, keep in mind that you must never force them to talk about something they don’t feel comfortable with.

Always consider the nature of the relationship you share with the person, and whether your questions are making them feel uncomfortable or not. The whole point of this exercise is to know someone on a more intimate level, not to disturb them emotionally or revel in their insecurities. Always acknowledge and respect the boundaries of others, and make sure that you are okay too if they choose not to answer any question. Sometimes their silence will tell you more than what their answer ever could.

Related: 50 Questions To Ask Yourself To Know Your Deepest Insecurities

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

1. Do you ever do anything just for getting attention? If yes, then what?

2. What is that one thing people assume about you, that you wish was true?

3. Which one would you prefer – manipulating someone, or be manipulated?

4. Have you ever thrown anybody under the bus to protect yourself and your personal interests?

5. How often do you pretend to be happy, even if you are not?

6. What is your ideal plan for avoiding difficult situations?

7. When was the last time you felt insecure about the things you pretend don’t make you insecure at all?

8. What is the one thing that puts you off about the dating scene nowadays?

9. What is the most challenging part of being in a committed, monogamous relationship?

10. Are you innately a very competitive person, but you pretend otherwise so that people like you more?

11. If given the option, would you want to know what your future looks like?

12. How do you really feel when someone doesn’t like you as a person?

questions insecurities self-sabotage

13. Do you feel angry and vindictive about the people who have betrayed and wronged you in the past?

14. For you, is revenge more important than peace?

15. Does it bother you when you are ignored by others or do you genuinely like to be left alone?

16. According to you, what’s the most exciting and best thing about flirting?

17. How do you manage your emotions, when you feel exceptionally jealous?

Related: 30+ Weird Questions To Get To Know Someone Better

18. Have you ever taken advantage of a good person, and then regretted it later?

19. Who is the first person you will run to if you are in any kind of trouble?

20. What is your worst and most painful memory to date?

21. Do you ever feel scared of being happy, because you always think that if you are too happy, it will get jinxed and something bad will happen?

22. If any of your ex-partners wanted to get back together with you, how would you react?

23. What is the one thing that people think about you, that you wish was untrue?

24. When you were a child, who scared you the most and made you feel anxious whenever they were around?

25. Which people, and what incidents that happened in the past, made you put up walls around yourself?

26. Have you ever lied to protect your reputation?

Related: 4 Steps To Move On And Heal Your Emotional Baggage

27. Are you scared of intimacy, especially emotional intimacy?

28. Are you scared of intimacy or are you scared of commitment?

29. Have you ever been just friends with an ex?

30. If money was no object, what was the first thing you would do?

31. What’s that one thing you feel you are really good at?

32. What’s that one thing you feel you are really bad at and wish to improve on?

33. What is that one country you want to travel to at least once before you die, and why?

34. What is the first thing you notice when you meet someone for the first time?

35. Have you ever loved someone so much, that you were willing to sacrifice anything and everything for them?

36. Do you have any fantasies that might be considered taboo?

37. Which emotion inspires you the most, whenever you feel like giving up?

38. How do you feel when someone criticizes you, even if it’s constructive criticism?

39. What is the one thing you will never compromise on, when in a relationship?

40. What is the one emotion that makes you want to give up and run away from everything?

41. Do you find it hard to say ‘no’ to things that you don’t love doing, just for the sake of pleasing other people?

42. Who do you hate the most in this world?

43. Do you think there’s really an afterlife?

44. Have you ever felt that it won’t make any difference to anyone if you die tomorrow?

Related: 50 Deep Questions That Can Strengthen Intimacy In Your Relationship

45. Are you good at holding yourself accountable for your mistakes, or do you have a hard time coming to terms with your blunders?

46. Do you often feel like you are not good enough?

47. What is the one thing you would never want your loved ones to know about you because you are ashamed of it?


48. What is the most absurd reason you have disliked someone?

49. What is the most absurd reason you have really liked someone?

50. How do you really feel when someone you love and care about, betrays you and your trust?

51. Do you feel comfortable with solitude, or does it make you feel empty and depressed?

52. If it was your last day on Earth, what are the things you would do before dying?

53. Do you harbor any opinions that you don’t openly express because you know they are judgemental and archaic? If yes, what are they?

54. Have you ever been physically violent with anyone?

55. Have you ever been arrested?

56. Are you happier when you are single or when you are in a relationship?

57. What’s the one thing you wish you could change about yourself, but find it very hard to?

58. Do you secretly like being controlling?

Related: 18 Reminders After A Relationship Ends and You Are Hurting

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?

Related: 9 Psychological Tricks To Make Someone Like You Instantly

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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