ANSWERS: 3
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watch the 40 year old virgin!!! just kidding, get her some magazines like elle, cosmo, latina, and browse the pictures with her, then ask if she wants a makeover? Sounds like she might fight you on that if she is sensitive, but make it like a fun time and then in her new make up and gear, fo out to a movie or restaurant or to the mall so she can get used to her new look. If someone notices her, compliment her on it.
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Mabie help her feel better about herself by taking her shopping or out to eat. do you know any single men her age? if so introduce them. =]
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Invite her to go on a girl's day out with you. Get your hair, makeup, and nails done. Then go together and get new outfits. This should help with her confidence. Don't just outright ask her if she "wants a makeover." That's offensive. Be her friend, and eventually you can give her less-subtle advice. Then maybe suggest she join an online dating site (there are free ones like okcupid.com) that might be more comfortable for her than meeting guys in person initially.
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