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Kerry Washington

In 2007, Kerry Washington broke up with her fiancé of three years, David Moscow, whom she admits to having left in order to find herself – and her fame apparently. By the time Kerry dropped him, she had become widely recognized (and highly compensated) for her roles in award-winning movies like Ray and The Last King of Scotland.

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Megan Fox

Before the pouty lips and Transformers movies, Megan Fox was just a struggling actress looking for a break. She lucked up in 2003 when she met and began dating 7th Heaven star David Gallagher who frequently brought her along to Hollywood parties and Lakers games. But though David is probably responsible for Megan’s come-up, she dumped him upon landing her first film role, then shacked up with Beverly Hills 90210 star Brian Austin Green shortly after.

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Olivia Wilde

At just 19-years old, Olivia Wilde married Italian filmmaker and musician Tao Ruspoli, but divorced him in 2011 (soon after she’d gotten her big break playing Quorra in Tron: Legacy). She then embarked on a series of high-profile relationships with A-list stars like Ryan Gosling, Justin Timberlake and Bradley Cooper before settling down with now-fiancé Jason Sudeikis.

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Mo’Nique

Mo’Nique wasn’t always in a ridiculous-sounding open marriage with Sidney Hicks. While she was still just a comedienne on the come-up, she met and married Mark Davis Jackson, the father of her 23-year old son, but dumped him around the time her role as Nikki on The Parkers began garnering her big time fame.

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Mila Kunis

Before becoming a fixture on the Maxim Hot 100 List, Mila Kunis was just the ditzy girl from That ’70s Show who dated co-star Danny Masterson. But upon scoring mainstream fame and eventually big time movie roles, Mila dumped Danny like a hot potato, ultimately opting for her more A-list co-star, Ashton Kutcher.