When: 1999

Age: 23

Reese Witherspoon met Ryan Phillippe at her 21st birthday party in 1997. The two hit it off immediately and by December 1998, they were engaged. After co-starring in Cruel Intentions, the Hollywood pair wed in June 1999. Two kids and seven years later, Witherspoon filed for divorce in November 2006, citing irreconcilable differences. "I don't think I realized how little I was living,” the actress dished in an ELLE magazine interview. “I was so consumed with trying to hold things together." Witherspoon moved on with Jake Gyllenhaal before marrying Jim Toth in March 2011.