Ryan Phillippe & Reese Witherspoon

Ryan Phillippe and Reese Witherspoon were once one of the most followed Hollywood couples in the ’90s. They initially met at Witherspoon’s 21st birthday party in 1997 and subsequently began dating. Two years later, they starred opposite each other in the 1999 hit film Cruel Intentions portraying Sebastian Valmont and Annette Hargrove. Just a few months after the premiere of the film, Phillippe and Witherspoon tied the knot. They welcomed their first child, a daughter named Ava Gardner, in 1999, and was then followed by their son, Deacon in 2003.

Despite being a famous couple, the two decided to lawyer up and go their separate ways in 2006, settling and sharing a joint custody of their kids. Although they are separated, Phillippe and Witherspoon have an excellent co-parenting relationship. The former is not romantically involved with anyone as of this year, while Witherspoon has been married to Jim Toth since 2011.