Ryan Phillippe's Romantic History
Credit: Mike Guastella/WireImage
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Reese Witherspoon
The couple and Cruel Intentions costars met in 1997 and wed two years later in Charleston, South Carolina. They have two children: Ava (September 1999) and Deacon (October 2003). Though Witherspoon filed for divorce in 2006, she and Phillippe remain on good terms.