I got over my shyness many years ago (well, I'd call it a mild social phobia, but essentially the same) and no harm has come out of it. In fact it's only resulted in a lot more friends and made conversations with newly acquainted girls stupid easy.
I realize that there are many different levels of shyness and those of some are deeper than others, but it's simple-- you just have to take a more cynical approach to things. I've realized that most people out there have very shallow personalities, are indifferent, bucketheaded, possibly boring-- and honestly... I couldn't give any f%@k less what they think about me.
The problem people have with shyness is that they're overly self-conscious about how others perceive them as a result of low self-esteem. So ask yourself now, "WHY do I care so much about what others think about me?"
What have these people whom you've yet to make contact done for you?
Absolutely nothing. The significance of those people in your life will still be zero whether you're too timid to approach them, or you DO approach them, make conversation and they dislike you (which has never happened to me.)
I don't know about you, but I would much rather risk being shot down than shug it off when I could have made some friends or met a special someone by simply joining in.
As for making conversations easier with chicks, it's the same who-gives-a-damn approach, and is an absolute must because you want to seem secure if you want a piece of the cake. You can either go up to them, be yourself, and maybe walk away with a number... or you can continue to be a self-contained waste of space.
Chances are you're not the same dry and ditzzy person that 80% of girls are beyond their looks, so what's the worry? Try to be less critical of your thoughts on what to say, replace that wasted thinking with humor, don't blabber on about Pokemon or some other lame crap and most girls are going to be interested in what you have to say and where it goes from there is up to you.
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