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Hilary Duff

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In July 2004, a then 17-year-old Duff began dating 25-year-old Good Charlotte rocker Joel Madden and changed her image to match the older man on her arm. H-Duff got super slim, had a full set of porcelain veneers capped onto her teeth and started dressing in much more sophisticated designer duds. Add chic hair and makeup, and you could barely tell the age difference between her and her older man.

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