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OP, I would consider myself quite shy and always have to force myself to talk to others.If you were to ask anyone though they would say I'm very outgoing.
I meanwhile am the one that stands in the background looking on..
Needless to say I don't have the best of "luck" so to speak...
I had negative self appraisals such as "ah I won't bother, they probably don't want to talk to me" etc. Then one day I just said "f this", jumped up and strolled over to someone, introduced myself and got chatting.
It was a relief and once you do it once it's easier as you start building a bedrock of confidence.
You gotta switch from worrying about what the women think of you and just focus on your own good time with your mates, don't care as much, see what your friends do and try pick up a few things.