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You basically have to compliment her on something she wants to be appreciated for, which others do not normally see in her. That's where the magic happens.
Yes. This advice has been given in "Art of Seduction" actually (for those that discredit the book, hehe).
A truly beautiful woman gets compliments that she's beautiful left to right. But, how often does she get compliments about her intellect, her success, etc.?
What is a beautiful woman insecure about? Is it her looks? Not necessarily. Most beautiful women know they are beautiful.
Find an area in her life where she's lacking, she's got low confidence in.
Let's say she's a hairdresser. Tell her her conversations are interesting, she's got a mind of her own, she's well-read (hopefully), she's one of the few women you've connected with on an intellectual level, or tell her that you respect/admire her trade, her business, etc.
Let's say she's an average looking woman but has a good career. She's most likely confident in that area of her life, but is she confident in her looks area?
She's a 6, but make her feel like a 10. Then she'll be hooked onto you to fill up this hole in her life.
She's getting older? Tell her oh, really, I thought you were much younger!
As an example: I had a friend that was overly sensitive about her looks. Face-wise and body-wise, she's around a 6, tops a 7 with make-up. She thought she'd never find a man. Well, she did. You should hear the comments he makes about her- you're so beautiful, you've got such great legs, any woman would kill to have your ass, etc. They got married. She told me one day she never thought how good looking she was until she met her man. She's made a number of comments where she goes, look at me, I'm such a hottie, aren't I....