Reese Witherspoon and Ryan Phillippe’s Ups and Downs Over the Years

Once one of Hollywood’s most beloved couples, Reese Witherspoon and Ryan Phillippe called it quits in 2006 after seven years of marriage — but the twosome are forever linked thanks to their look-alike children.

While many believe that the twosome met and fell in love while filming the 1999 movie Cruel Intentions, Witherspoon confirmed on Watch What Happens Live With Andy Cohen in 2015 that they had been “living together for about a year and a half” when they shot the film. She also told Andy Cohen at the time that daughter Ava and son Deacon hadn’t seen the movie.

“They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she said at the time. “Not interested.”

Phillippe, meanwhile, recalled telling their kids about making the movie during a 2014 HuffPost Live interview.

“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,” he said, noting that the former spouses were in a “really great place” at the time. “It’s a feeling-out process. … It’s going well, and she’s happy and remarried, and our kids are incredible. I’m proud of the way we’ve handled it and who our little people are.”

It wasn’t always smooth sailing for the twosome, however. When news of their split broke in 2006, Phillippe was accused of cheating on Witherspoon with Stop-Loss costar 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 a statement in November 2006.

Phillippe and Cornish went on to date until February 2010. He later welcomed a daughter with then-girlfriend Alexis Knapp in 2011. Witherspoon, for her part, married talent agent Jim Toth and gave birth to son Tennessee in September 2012. Witherspoon and Toth announced in March 2023 that they were divorcing after nearly 12 years of marriage.

In 2014, the Big Little Lies star recalled how her split from Phillippe — which came months after she won her first Oscar — affected her career.

"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,” Witherspoon said on 60 Minutes. “You know, you can't really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn't making things I was passionate about, I was just kinda working. It was really clear the audiences weren't responding to anything I was putting out there."

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Scroll through for a timeline of Witherspoon and Phillippe’s ups and downs: