Reese Witherspoon and Ryan Phillippe
The Cruel Intentions costars — who share daughter Ava and son Deacon — announced their split in 2006 after seven years of marriage. The Big Little Lies actress filed for divorce thereafter.
That same year, the Shooter alum began dating his Stop-Loss costar Abbie Cornish following rumors of an alleged affair. Phillippe dated Cornish until early 2010 and then went on to welcome a daughter with Pitch Perfect actress Alexis Knapp in 2011. He then dated fiancée Paulina Slagter for five years before breaking off their engagement in 2016.
Witherspoon, meanwhile, wed Jim Toth in 2011. They are the parents of son Tennessee.Back to top