Ryan Phillippe

Remember the ’90s heartthrob Ryan Phillippe? He starred in I Know What You Did Last Summer, The Lincoln Lawyer, and Cruel Intentions－the latter being the film where he and former wife Reese Witherspoon developed a relationship. The two young stars got married back in 1999, and their daughter, Ava Elizabeth, was born soon after on September 9, 1999.

Phillippe was 25 years old when he became a first-time father. His and Witherspoon’s second child, Deacon, was born in 2003. However, on October 30, 2006, he and the Legally Blonde actress formally separated. The former couple now claims that they have mastered the art of co-parenting to a certain degree. Recently, they reunited to throw a small backyard party for Deacon’s 17th birthday. Both Phillippe and Witherspoon posted sweet and thoughtful video greetings for their son on their social media accounts.