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stop being self concious.. drop the glasses .. put on a cool shirt.. put some hair styling agent in your hair and go ...
idk if he should give himself a makeover, I just think you should focus on the girls your talking to and not your looks. When I'm talking to a girl I'm 100% focused on gaming her, If you came up to me while I was talking to a girl and asked me what color my hair is I couldn't tell you.
I have glasses, I wear the same jacket almost everyday, my hair is as normal and flat as can be; but I never notice so the girls don't.
Glasses can be used very well; you can talk about them to draw her attention to your face, you can talk about how 'different' you look with them off and have her spend some time giving you kino to try to take them off of you. Contacts arn't special, they're normal and how many girls want a 'normal' guy?