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What insecurities/fears hold you back from talking/approaching people

This one is in the title really - what insecurities about yourself or fears you hold stop you from approaching people? Whether it's to make a new friend or to try to and grab the number of the person you've got a crush on, what's stopping you? For me, I have a general fear that I will either scare people away with my very dark humour or I'll bore them to death as I generally seem to fall into a trap of trying to one-up people by saying what I've done even though I really don't actively try to do that!

Socially as well, I find it very hard to find what people are doing/thinking and whether it's the right time to approach them. There's been many a time I've stood in a corridor at work waiting for someone to notice me as opposed to me just saying "Excuse me..." - I just don't want to interrupt. What's holding you back? How did you overcome that (if you did)?
 
For me it's a case of social anxiety and social awkwardness that just stops me dead in my tracks. If I'm around too many people I cannot function, at all. If I'm around people I know, it's a different story and I can almost be sociable, but groups, particularly groups of strangers, I'm stoic and shut down.

As for what stops me with things like approaching people or asking a crush for their number, I think for me that's all down to my own self-hatred and self-loathing issues. I have many, many triggers that can make me spiral inwardly, and I've got a complicated history with my mother and her hatred towards men that's made me uncomfortable "being a man" around women, so I'm a shy, timid person who hates himself and gets triggered into very dark places very easily. It's exceptionally difficult to tell people how you feel about them when you're barely holding your self together and simultaneously wishing you would crumble.
 
I do not have any charm. I pass as a regular ordinary person. That is not helping when you are working in customer care. That is one reason I moved on. I never liked that job. There is nothing wrong with the job or my attitude. The job itself demands dealing with rude people. They call it " challenging customers " and hide all the rudeness they come with.
 
I know we got those who are simply introverts, you hardly see them associating with others in a public settings. Due to their indoor lifestyle made them develop paranoia which made them uneasy to communicate effectively.
 
I have difficulties with approaching people. I always thought I was shy and reticent. However, looks like I have a social anxiety disorder. I have never been into therapy for this disorder.
 
I don't like it that I might not make my question or statement very clear. Then I have to stay and talk with them longer to clarify and that's annoying.
 
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