Ryan Phillippe Shares Throwback Snap with Ex Reese Witherspoon 'Drenched in Late '90s Angst': 'We Were Hot'

Phillippe and Witherspoon were married in June 1999 and welcomed two kids before their 2006 split: daughter Ava, 24, and son Deacon, 20

Ryan Phillippe is throwing it back with Reese Witherspoon!

On Monday, May 27, the actor shared a photo with his ex to his Instagram Stories, which showed them decked out in quintessential '90s style with their arms wrapped around one another.

Witherspoon, 48, had her blonde hair cut in a chin-length chopped style and wore a body-hugging, black-and-white striped dress featuring a high neckline with a necktie-style detail.

Meanwhile, Phillippe, 49, rocked a sleeveless collared blue-and-white-striped shirt, black slacks and dark sunglasses, as well as a mohawk hairstyle.

"We were hot and drenched in late 90's angst @reesewitherpoon (such a cooler time than today)," Phillippe wrote below the image.

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Related: Reese Witherspoon and Ryan Phillippe's Relationship: A Look Back

Phillippe first met Witherspoon at the actress's 21st birthday party in 1997, before working together on the movie Cruel Intentions. They tied the knot in Charleston, South Carolina, in June 1999. At the time, Witherspoon was several months pregnant with their daughter Ava Phillippe, now 24.

During the course of their marriage, they welcomed two children together: their daughter Ava in 1999 and son Deacon Phillippe, now 20, in 2003.

In October 2006, Phillippe and Witherspoon announced they were splitting up in a joint statement. "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."

Not long after his marriage ended, Phillippe revealed in an interview with W magazine that the divorce 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," the Prey star added. "It was the worst time of my life."

Related: Ryan Phillippe Says He Feels 'More at Peace' at This Stage in Life: 'I Spent a Lot of Time in Prayer'

Following their divorce, Witherspoon and Phillippe have continued to co-parent their children, most recently celebrating Deacon's high school graduation together in June 2022.

Speaking about his co-parenting relationship with Witherspoon, Phillippe told Entertainment Tonight back in November 2016, “You have to get to that point as a divorced parent, as any parent, where you’re not putting yourself first."

“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.

In addition to Ava and Deacon, Witherspoon is mom to 11-year-old son Tennessee, whom she shares with ex Jim Toth. The Legally Blonde actress tied the knot with Toth, 53, in March 2011, and they announced their split in March 2023.

Phillippe never remarried, but shares 12-year-old daughter Kai with ex-girlfriend Alexis Knapp. He and the Pitch Perfect actress, 34, briefly dated in 2010.

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