Ryan Phillippe took a nostalgic trip down memory lane by sharing a throwback photo with his ex-wife Reese Witherspoon. The snapshot, posted on his Instagram Stories on Monday, May 27, captured the pair embracing in typical ’90s fashion.

In the photo, Witherspoon, 48, sported a trendy chin-length haircut and a form-fitting black-and-white striped dress, while Phillippe, 49, rocked a sleeveless blue-and-white-striped shirt, black trousers, and a stylish mohawk.

Phillippe and Witherspoon first crossed paths at the actress’s 21st birthday bash in 1997 before co-starring in the film Cruel Intentions. They exchanged vows in June 1999 in Charleston, South Carolina, while Witherspoon was expecting their first child, Ava Phillippe, who is now 24.

During their marriage, the couple welcomed two children: Ava in 1999 and son Deacon Phillippe, now 20, in 2003. However, in October 2006, they announced their separation, emphasizing their commitment to co-parenting and urging privacy and respect for their family.

Phillippe later opened up about the emotional toll of their divorce, describing it as “the darkest, saddest place” he had ever experienced. Despite the challenges, they prioritized their children and maintained a strong co-parenting dynamic.

Witherspoon went on to marry Jim Toth in March 2011, with whom she shares an 11-year-old son named Tennessee. However, they announced their split in March 2023.

Phillippe, on the other hand, never remarried but shares a 12-year-old daughter named Kai with his ex-girlfriend Alexis Knapp. Their relationship briefly flourished in 2010.