Ryan Phillipe & Reese Witherspoon
Believe it or not, Reese Witherspoon and Ryan Phillippe met the old-fashioned way in 1997, at Reese’s 21st birthday party! Love was in the air, and a year and a half later they were married.
The same year they were married, 1999, the couple played starring roles in the film Cruel Intentions. There are probably not many better tests for a young marriage than working together on a film set. Yikes. The couple has two children together. Sometimes even true love comes to an end and the couple separated in 2006.