Ryan Phillippe Posts a Flirty Throwback of His Ex-Wife, Reese Witherspoon: ‘We Were Hot’

Is Ryan Phillippe shooting his shot with his ex-wife, Reese Witherspoon?

On May 27, the 49-year-old actor threw us all the way back to 2001, posting a photo from a Legally Blonde party he attended with Witherspoon. The former couple met on the set of Cruel Intentions in 1997 and tied the knot in 1999. They split in 2006 and share two children: Ava, 24, and Deacon, 20.

Now, Phillippe is reminiscing about the good old days. “We were hot and drenched in late-’90s angst,” he captioned the throwback snap on his Instagram Story, directly tagging his ex. In parenthesis, he described that era as “such a cooler time than today.” For her part, Witherspoon has not yet replied to the post…at least on social media.

So, was this message a blatant attempt at flirting or was Phillippe simply stating facts? The former couple did look particularly striking in the photo, with Witherspoon rocking a chic chin-length bob and body-hugging striped dress while Phillippe appeared brooding with his cropped mohawk and aviator sunglasses. Then again, it’s slightly hard to pull off “late-90’s angst” in a striped sleeveless polo… In his defense, they were in the Hamptons!

Ryan Phillippe and Reese Witherspoon on July 7, 2001.

RJ Capak

Five years after her first divorce, Reese Witherspoon got married to Hollywood producer Jim Toth, with whom she shares an 11-year-old son. However, The Morning Show star is currently single, at least as far as the public is concerned.

Witherspoon and Toth announced their own split with a joint statement in March 2023. “It is with a great deal of care and consideration that we have made the difficult decision to divorce,” they wrote in the since-deleted Instagram post. “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.”

They continued, “Our biggest priority is our son and our entire family as we navigate this next chapter. These matters are never easy and extremely personal. We truly appreciate everyone’s respect for our family’s privacy at this time.”

Although Ryan Phillippe has since been linked to multiple partners and welcomed another daughter in 2011, the actor never remarried and appears to be single. A few years after his divorce, Phillippe referred to his split from Witherspoon as “the darkest, saddest place I had ever been.”

“There were a good four or five months of not being able to get out of bed,” he told W Magazine in 2008, per People. “It was the worst time of my life.”