Reese Witherspoon and Ryan Phillippe
The pair first met on the set of Cruel Intentions in 1999 and tied the knot that June. They later divorced in June 2008, but continue to share daughter Ava and son Deacon. In 2011, Witherspoon remarried to CAA agent Jim Toth; the couple welcomed their first child together, son Tennessee, in September 2012. Phillippe also welcomed a baby girl with ex-girlfriend and Pitch Perfect actress Alexis Knapp in July 2011.