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The Makedown (2009)

Anna Norton grew up as an unattractive, fat and nerdy girl from Ohio. Even attending an Ivy League college didn't help her gain friends or self-confidence. She moves to New York, where her new boss, Janice, a caterer, gives her a makeover, helping her lose weight and improve her appearance. Then Anna falls for Ben, a gorgeous lawyer, and amazingly he becomes her boyfriend. But he's extremely flirtatious and still out of her league, so to keep other women away, she begins to diminish his good looks through the reverse makeover - the Makedown. An intriguing concept told with edgy humour but the character is as unappealing on the inside.

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