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10Reese Witherspoon, Ryan Phillippe, Abbie Cornish

When the movie Cruel Intentions hit cinemas in 1999, Ryan Phillippe and Reese Witherspoon, who both starred in it, were already an item. By the time the film was released, they were engaged to be married and Witherspoon was

several months pregnant with their first child. Despite the concern of many that the couple was too young to marry, they beat the odds and had a seemingly solid marriage. Eight years and two children later, however, the couple decided to separate. It was rumored that Phillippe was caught cheating on his wife with his Stop-Loss co-star, Abbie Cornish. He started a relationship with Cornish while his divorce was being processed.

Next 9 Heather Locklear, Richie Sambora, Denise Richards

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