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ryan phillippe reese witherspoon 2005© Getty Images

Ryan Phillippe shares 'hot' throwback photo with single ex-wife Reese Witherspoon

The Cruel Intentions stars were married for nine years

Jenni McKnight
US Lifestyle Editor
May 28, 2024
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Ryan Phillippe took a trip down memory lane and shared a "hot" throwback photo with his ex-wife Reese Witherspoon.

The 49-year-old threw it back to the '90s and posted a gorgeous photo of the former couple with their arms wrapped around each other.

In the image, Ryan is wearing a sleeveless blue-and-white-striped collared shirt with black pants and aviator sunglasses while rocking a mohawk hairstyle.

Reese, meanwhile, echoed Ryan in a black-and-white striped dress that featured a high neckline, red buttons, and a figure-hugging silhouette – and she looked gorgeous with her chin-length bob.

"We were hot and drenched in late 90's angst @reesewitherspoon. (such a cooler time than today)," he captioned the photo on his Instagram Story on Monday.

Ryan and Reese first met at the Oscar-winning actress' 21st birthday party in 1997 and two years later they worked together on Cruel Intentions.

ryan phillippe reese witherspoon 90s throwback photo© Instagram
Ryan and Reese married in 1999

They married in June 1999 in Charleston, South Carolina when Reese was several months pregnant, and announced their separation in October 2006 after nine years of marriage.

"We are saddened to announce that Reese and Ryan have decided to formally separate," a rep for the couple said. 

"They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time."

Ryan Phillippe and Reese Witherspoon at the Kodak Theatre in Hollywood, California © Getty Images
Ryan and Reese were married for 9 years

Reflecting on the divorce in an interview with W magazine, Ryan said: "It was the darkest, saddest place I've ever been. There were a good four or five months of not being able to get out of bed. It was the worst time of my life."

Despite the challenges, the couple has continued to co-parent their children, daughter Ava, 24. and son Deacon, 20.

Reese with her daughter Ava and eldest son Deacon© Getty
Reese and Ryan share daughter Ava and son Deacon

"You have to get to that point as a divorced parent, as any parent, where you're not putting yourself first," Ryan told Entertainment Tonight about his and Reese's co-parenting relationship.

"You want the kids' experience to be its own and not like, 'Well, I need to have my time!' We have been very good about that," he added.

reese witherspoon ryan phillippe deacon© Instagram
Ryan and Reese successfully co-parent their kids

Ryan never remarried after his divorce from Reese, but he did welcome another child, daughter Kai, 12, with his ex-girlfriend Alexis Knapp.

Reese went on to marry Jim Toth after a whirlwind romance in 2011 and told Marie Claire that she felt "a great sense of relief and an incredible amount of support from my husband".

Together they welcomed their son Tennessee, now 11. Reese and Jim announced their split in March 2023 after 12 years of marriage.

reese witherspoon jim toth screen actors guild awards 2020© Getty Images
Reese and Jim split in March 2023

In a joint statement, they said: "We have some personal news to share... It is with a great deal of care and consideration that we have made the difficult decision to divorce."

They added: "We have enjoyed so many wonderful years together and are moving forward with deep love, kindness, and mutual respect for everything we have created together."

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