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what i've found generally works, because it seems though almost every woman in the world who is not a supermodel has self esteem issues *cough*go figure*cough*... anyway what i found works is something that she can't refute... say something like "you're beautiful to me", or "doesn't matter how you look, you're always beautiful to me"... things like that strike a romantic nerve and even if she doesn't believe that she's beautiful at first, she's still going to be comforted by you.
also, you have to TREAT her like she's beautiful (not to be patronizing). It's kind of vague advice really, but if you do things that make her feel beautiful without words... like maybe take pictures a lot (lurkette:-p)
i hope that helps a little bit, it's just my two cents.
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In the end we are but wisps
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