Ryan Phillippe and Abbie Cornish
Phillippe's first serious relationship post-Witherspoon was with his Stop-Loss co-star, Abbie Cornish. Their relationship abruptly ended in 2010.
"I have a new rule: not to date anyone who has a publicist," he told Howard Stern in 2011 of their split. "Who announces a breakup? I don't understand that!"
Photo Credit: WENN.com