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Ryan Phillippe Posts Oddly Flirty Throwback Photo Of Him And Ex, Reese Witherspoon

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His intentions don’t seem cruel — but what are they?

On Monday, Ryan Phillippe posted a throwback photo of him and his ex-wife, Reese Witherspoon, on his Instagram Stories, People magazine reported.

The photo was taken in 2001, five years before their 2006 split, at a “Legally Blonde” party in South Hampton, New York. In the photo, the Oscar winner is sporting a short bob and wears a tight black-and-white striped dress, while Phillippe dons a striped sleeveless shirt with his hair in a fauxhawk.

A very similar image to the one Ryan Phillippe reportedly posted of him and Reese Witherspoon earlier this week.

RJ Capak via Getty Images

“We were hot and drenched in late 90′s angst @reesewitherpoon (such a cooler time than today),” Phillippe wrote below the image, according to People.

Although, arguably, the two look pretty much the same now.

Reese Witherspoon in April, and Ryan Phillippe in 2023.
Reese Witherspoon in April, and Ryan Phillippe in 2023.

The flirty caption — and decision to post a throwback photo of himself with his former wife for no specific reason — seems pretty loaded. Especially since Witherspoon announced her divorce from husband Jim Toth just a year ago.

Phillippe and Witherspoon met at the “Election” star’s 21st birthday party in 1997, then worked together on the 1999 movie “Cruel Intentions.” According to a 1998 interview Witherspoon gave to Jane magazine, via People, her first words to Phillippe upon meeting him at her birthday party were pretty spicy.

Witherspoon and Phillippe during the “54” premiere in 1998.
Witherspoon and Phillippe during the “54” premiere in 1998.

Steve Granitz via Getty Images

“I don’t know what came over me — maybe the seven Midori sours — but I told him, ‘I think you’re my birthday present,’” she told the magazine at the time. “He thought it was so flattering, and now that I think about it … how embarrassing!”

The two tied the knot in 1999 and announced their split in 2006. The former couple have two children, Ava, 24, and Deacon, 20.

After their divorce, Witherspoon went on to marry Toth, an actor and producer, in 2011, and the two welcomed son, Tennessee, now 11.

Phillippe never remarried but shares 12-year-old daughter Kai with ex-girlfriend and “Pitch Perfect” actor Alexis Knapp.

After his 2006 split from Witherspoon, Phillippe told W magazine in 2008 that it was “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,” the “Crash” star said at the time. “It was the worst time of my life.”

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