Ryan Phillippe and Reese Witherspoon
Ryan Phillippe and Reese Witherspoon were one of Hollywood's most beloved couples in the late '90s, but they split in 2006. The split was not pretty, but their relationship is better these days.
"It's gotten to a place where we're great friends and great co-parents...," he told Howard Stern in 2011. "After I had my breakup, she called, and after she did, I called . . . I trust her to make the right decisions around our children. I hope she feels the same way."
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