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Being shy can be difficult to overcome
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Being shy is hard to overcome but the building of self confidence can start easily by talking to people in large groups or putting in opinions when your around strangers (i used to be reallllllyyyyy shy to the point of i couldnt look at a girl without blushing) but i fixed that problem and over the years you learn to fit in and speak outloud to random strangers. I tend to do it too much so i got to much confidence which makes me an arse and a cocky Sob.
Girls will start talkin to you and i dont think it is a "Guys role" to ask the girl out i think if she wants to date me then she should ask me not the other way around.
All you need man is self confidence it builds the way you feel on the look of yourself and not question what is wrong with the way YOU are, learn to loosen up around strangers/girls and im sure you will be able to find someone who is willing to date you.