You seem to be too stuck in your head and worried about what other people think of you. You mentioned that you don't like talking about your shortcomings. I'm going to suggest that you fear being vulnerable because you fear the judgments of others. You like living in your comfort zone because no one will attack you there. So you find yourself in this nice, neat little box.
The way around a fear is through it. Do something every day that is beyond your comfort zone. The more you do this the more comfortable you will find yourself in your skin. In addition you will gain massive amounts of confidence in yourself because lack of confidence is an abundance of fear.
By doing things that are scary you will worry less what others think of you which means after a conversation is over, it's done. No more spending the entire night thinking if you said the right thing or the cool thing.
If you are a guy, I suggest taking a look at the article I wrote on my signature.
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