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

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?

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