Ryan Phillippe and Reese Witherspoon at the Soho Grand Hotel in New York on October 30, 2006
Ryan and Reese met at her 21st birthday party in 1997 and married two years later, in 1999. The couple, who have two children together, allegedly split after Reese uncovered evidence that Ryan was cheating on her with his Stop-Loss co-star Abbie Cornish, according to Us Weekly. Reese filed for divorce in 2006, at which point Ryan and Abbie took their relationship public. Abbie broke up with Ryan in early 2010 amidst rumors that he was cheating on her with Heroes star Hayden Panettierre, reports Celebuzz.