Reese Witherspoon’s Ex-Husband Ryan Phillippe Revisits Their ‘Hot’ ‘90s Relationship

Ryan Phillippe is revisiting his relationship with ex-wife Reese Whiterspoon by sharing photos of the two in the ‘90s via an Instagram Story.

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Reese Witherspoon and Ryan Phillippe
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Ryan Phillippe took to his Instagram Stories to reminisce on his relationship with ex-wife Reese Witherspoon on Monday, May 27. ”We were hot and drenched in late 90’s angst @reesewitherpoon (such a cooler time than today),” wrote the 49-year-old actor.

The Instagram Story showcased a snap of the then-couple from the 2001 Legally Blonde party at the Hamptons wrapped in each other’s arms in striped outfits. The actress, who played Elle Woods in the movie, was wearing a black and white striped halter dress and Ryan was in a blue and white striped tank top with gray pants, topped off with sunglasses.

While bringing back the good old times, he shared a picture of his then mohawk, which he rocked in 1995 to The Smashing Pumpkins’ “Bullet with Butterfly Wings.”

The former couple met back on the set of Cruel Intentions. They tied the knot in 1999. During this time, the two welcomed Ava — in 1999 — and Deacon Phillippe — in 2003. 

Ryan Phillippe and Reese Witherspoon
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During a 2015 interview with Watch What Happens Live With Andy Cohen, the 48-year-old actress mentioned, “It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [in New York City], so there we were with Ava and Deacon talking, and they were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds.”

Amid their split in 2006, Ryan was accused of cheating on the Morning Show actress with his Stop-Loss co-star Abbie Cornish. “I’m not a perfect person, but I’m not guilty of a lot of the things I have been accused of. My priority is and always has been the health and safety of my family,” he said.

In 2014, Reese recalled her separation from Ryan on 60 Minutes. “Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better,” she expressed.

Since the breakup, the two focused on growing their families. Reese was married to Jim Toth from 2011 to 2023. Throughout their time together, they welcomed son Tennessee in September 2011. Ryan on the other hand, though he never remarried, did welcome daughter Kai with his ex Alexis Knapp in 2011.