The young stars' meet-cute eventually led to marriage. The pair tied the knot in June 1999. Reese was just 23 at the time, while Ryan was 25. They welcomed two children together, Ava Phillippe ...

Witherspoon and actor Ryan Phillippe even starred in a film together, the cult hit Cruel Intentions. The former couple was married for seven years before finally splitting in 2006. They continued to ...