Ryan Phillippe has had his fair share of high-profile romances — but coparenting remains his top priority.
The Shooter star started dating Reese Witherspoon in 1997 after meeting on the set of Cruel Intentions. They wed two years later in South Carolina and welcomed daughter Ava and son Deacon in September 1999 and October 2003, respectively. After less than a decade of marriage, the pair called it quits in 2006 when Witherspoon filed for divorce, citing irreconcilable differences as the reason for the split.
In 2014, Phillippe looked back on filming the erotic drama — and praised the relationship he and his ex-wife have cultivated while raising their two children.
“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,” the Lincoln Lawyer told the HuffPost in 2014, 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.”
Following his divorce from the Witherspoon, Phillippe moved on with Abbie Cornish, whom he was with for four years before their 2010 split. He was later briefly linked to Rihanna and Amanda Seyfried before on-off girlfriend Alexis Knapp gave birth to their daughter, Kai.
While the pair only dated for a few months in 2010, a source exclusively told Us Weekly that the Setup star was in the delivery room when the model gave birth in July 2011.
“She looks like moi. A lot more so now,” Knapp told E! News in June 2012. “They always come out looking like the dads, because men are just fat and puffy and can’t open their eyes too much.”
Less than a year after his breakup with Knapp, Phillippe made his red carpet debut with Paulina Slagter. The pair got engaged in December 2015, but called it quits less than a year later. The Delaware native then began dating Elise Hewitt. The twosome were together for just three months before she filed a $1 million lawsuit against Phillippe, in which claimed he physically abused her in his home in California.
The Damages alum, for his part, denied the allegations.
“As a staunch advocate for the health, well-being and equality of women, Ryan is completely devastated that these false allegations have been made and circulated,” the actor’s rep told Us in a statement at the time. “Domestic violence is an incredibly serious issue and fabricated and proven false claims should not be used to unjustly slander the falsely accused. The claims are false.”
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Keep scrolling for Phillippe’s complete dating history:
The Cruel Intentions costars met in 1997 and wed two years later in Charleston, South Carolina. They share two children: Ava and Deacon. Though Witherspoon filed for divorce in 2006, she and Phillippe remain on good terms.
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The couple met on the set of their film Stop-Loss and began dating in 2006, shortly after Phillippe and Witherspoon announced their separation. After four years together, Us confirmed the pair had called it quits. “He called her to end the relationship,” a source shared at the time. “They had grown apart.”
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Phillippe was briefly linked to the Twilight star in February 2007 after they were spotted out together in Los Angeles.
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The Crash star and the So Undercover actress began dating in May 2010 but called it quits four months later. Knapp gave birth to their daughter, Kai, in July 2011.
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The twosome met at Kate Hudson’s Halloween party in October 2010 and were on and off for several months before calling it quits for good in June 2011. “It was mutual,” a source told Us at the time. “They were never fully committed.”
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The pair “initially hooked up” in December 2010 when the singer was on the rock with ex Matt Kemp, a source exclusively told Us at the time. However, the twosome never commented on their brief romance.
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In July 2011, it was revealed that the Lincoln Lawyer star had been getting “hot and heavy” with the multiplatinum singer. “They were just hooking up” a source told Us. “It was nothing serious.”
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The Big Sky alum was first linked to the model in February 2012. They made their red carpet debut three months later at a Hugo Boss event in Beijing, China, and later got engaged in December 2015.
“She’s awesome,” Phillippe gushed of his then-fiancée during an interview with Howard Stern at the time. “When people see her they have these judgments because she could be a model, but she’s about to graduate Stanford Law. … As you get older certain issues become more important to you. I’m very involved in civil rights issues, and so to be with a woman who could actually make an impact in the legal realm — that’s a beautiful thing.”
In 2016, the duo called off their engagement after five years together.
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Phillippe briefly sparked romance speculation with a second Twilight actress in 2013 after meeting Greene on the set of their film One Shot.
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Phillippe and Hewitt dated for two months in 2017. After their split, the Playboy model filed a $1 million lawsuit against the former teen idol, claiming he physically abused her at his home in California. According to documents obtained by Us at the time, Hewitt was subsequently hospitalized at Cedars-Sinai Medical Center in Los Angeles. She obtained an emergency protective order against Phillippe to keep him from coming within 100 yards of her.
Phillippe denied the allegations, with his rep telling Us in a statement that he was “completely devastated that the false allegations have been made and circulated.
The statement continued, “Domestic violence is an incredibly serious issue and fabricated and proven false claims should not be used to unjustly slander the falsely accused. The claims are false.”
The exes settled outside of court in October 2019, just four days before his assault case was due to come before a judge.
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