Ryan Phillippe’s Dating History: Reese Witherspoon, Rihanna and More

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 Cornishwhom 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 AND! 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 Butcher. 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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