As Cruel Intentions turns 20, here's a trip down memory lane to the relationship of stars Reese Witherspoon and Ryan Phillippe


Reese Witherspoon and Ryan Phillippe‘s electric chemistry in Cruel Intentions — which turns 20 on Tuesday — should come as no surprise: the pair were a real-life couple during the making of the teen sexual thriller.

While moviegoers were caught up in the 1999 boarding school drama that unfolded with their characters Sebastian and Annette onscreen, Witherspoon and Phillippe were well on their way to creating a family together.

The two met in 1997 at the actress’ 21st birthday party. The Big Little Lies actress recalled their meeting in a 1998 interview with Jane.

“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 admitted at the time. “He thought it was so flattering, and now that I think about it… how embarrassing!”

Just one year after they met, the two became engaged. Before walking down the aisle, though, Witherspoon became pregnant with their first child, daughter Ava, now 19.

Reese Witherspoon and Ryan Phillippe in Cruel Intentions
| Credit: Melissa Moseley/Columbia/Kobal/REX/Shutterstock

In 1999, Witherspoon and Phillippe tied the knot just three months after Cruel Intentions premiered — while she was six months pregnant — in an intimate ceremony in Charleston, South Carolina. Four years later, they welcomed their son Deacon, now 15.

The two announced they were separating in 2006 in a joint statement.

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the couple said at the time. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.”

In 2015, Phillippe told Larry King he believed the “problem was age.”

“When we got together we were so young,” he said at the time. “I think it can create issues with two people in this industry because there’s so much noise that goes along with it.”

Witherspoon echoed his sentiments in 2017 during an appearance on ITV’s Lorraine.

“I got married when I was 23 and I had two kids by the time I was 27,” she said. “So I don’t know, you know, sometimes it’s good to know yourself.”

William Morris Agency Pre Golden Globe Party
Credit: Alex J. Berliner/BEI/REX/Shutterstock

She added, “I would never change anything. I’ve said to my daughter, I think, you know, [at] 25, you start to know yourself a little bit better.”

Phillippe and Witherspoon discussed filming Cruel Intentions with their children in 2014.

The Shooter actor told HuffPost Live the four had a fun family moment while taking a walk in New York City’s Central Park — where key locations of the film were shot.

“It was funny — we were reminiscing then because we shot a lot of Cruel Intentions there 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,” Phillippe shared.

He revealed the two had a good relationship as co-parents.

“It’s going well,” he said at the time. “She’s happy and remarried and our kids are incredible. I’m proud of the way we handled it and who our little people are.”

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While the two split, they remained friendly while co-parenting their two children. Phillippe welcomed his third child, daughter Kai, in 2011 with then-girlfriend Alexis Knapp.

He then became engaged to Paulina Slagter but the two split in late 2016.

Witherspoon married talent agent Jim Toth in 2011, and the next year the two welcomed their son, Tennessee. The Oscar-winning actress has doubled down on producing projects she’s passionate about, including 2014’s Gone Girl and Wild, both of which she produced.

She starred in Wild as Cheryl Strayed and both films went on to become nominated for Academy Awards. Witherspoon also starred in and produced the HBO hit series Big Little Lies.

Cruel Intentions is returning to theaters nationwide for its 20th anniversary for one week only beginning March 22.