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Take this common scenario:

Billy is somewhat shy around women. He never really had luck with the opposite sex, and so he holds part of himself back when he is around women. When he sees a hot woman, he doesn't know what to say to her.

Given his shyness, he almost never makes the first contact with an attractive woman. After years and years teen chat avenue of this, and waiting for the woman to come and talk to him, he finally settles for a less attractive woman. Since he never got enough face time with women, he didn't get the experience that would have taught him how to charm and attract the kind of girl he wants.