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

The twosome met at Witherspoon’s 21st birthday in March 1997.

“I don't know what came over me — maybe the seven Midori sours — but I told [Ryan], 'I think you're my birthday present,’” she confessed to Jane magazine in 1998. “He thought it was so flattering, and now that I think about it … how embarrassing!"

Witherspoon and Phillippe starred in Cruel Intentions alongside Sarah Michelle Gellar and Selma Blair. The film hit theaters in March 1999.

Witherspoon and Phillippe exchanged vows in South Carolina in June 1999, less than a year after he popped the question.

The Election star gave birth to their daughter, Ava, in September 1999, three months after their nuptials.

The pair made headlines when Phillippe addressed their pay disparity while presenting with Witherspoon at the 74th Academy Awards.

“You make more than I do. Go ahead,” the actor replied after his then-wife asked if she could read the winner.

Nearly two decades later, Witherspoon admitted she was “flummoxed” by the remark.

“I forgot that ever happened. He did say that, and no, it wasn’t scripted. He didn’t tell me he was going to say that before it happened on air,” she explained on the “HFPA in Conversation” podcast.

The Legally Blonde star went on to share a story about Ava being “so embarrassed” in 2nd grade by a classmate discussing her mother’s success.

“I said, ‘Don’t ever feel ashamed of a woman making money.’ There are women all over this world who don’t have an opportunity or an education or the ability to make money,” she recalled. “The more women who make more money will give more money away, will take care of their societies, will take care of their communities, will do more with that money.”

The duo welcomed son Deacon in October 2003.

Witherspoon thanked Phillippe in her acceptance speech for Best Actress at the 78th Academy Awards in March 2006.

“I want to say thank you to my wonderful husband and my two children, who should be going to bed,” the Walk the Line star said. “And thank you for loving me so much and supporting me.”

Witherspoon and Phillippe announced their separation in October 2006 after seven years of marriage amid reports of his relationship with Cornish.

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the duo 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.”

The actress filed for divorce, citing irreconcilable differences, that November.

In their divorce docs, Witherspoon asked for physical custody of Ava and Deacon and visitation for Phillippe. In his response, the actor asked for joint legal custody and physical custody, which he was granted in October 2007.

While Witherspoon, who is one of Hollywood’s highest-paid actresses, and Phillippe didn’t sign a prenuptial agreement, he didn’t seek spousal support from her.

Phillippe and Cornish called it quits in February 2010. He later went off about their headline-making romance and split on Howard Stern that April.

"I have a new rule: not to date anyone who has a publicist. Who announces a breakup? I don't understand that! There's no need for that,” he said. "I've been dumped on in the press for relationship stuff since Reese and I divorced. I'm tired of getting s—t on. I don't feel like I deserve it. Things happen! How many people have you broken up with over your life?"

Phillippe also revealed that Witherspoon reached out to him after his split from Cornish — and he did the same after she split from Jake Gyllenhaal.

“It’s gotten to a place where we're great friends and great coparents,” he said.

Witherspoon married Toth in March 2011.

"I'm very happy for both Reese and Jim," Phillippe told the New York Daily News at the time. "I wish nothing but the best for the mother of my children."

After their wedding, the Shooter star was often spotted watching Deacon play soccer with the couple.

Witherspoon made headlines in April 2013 after she was arrested for a count of disorderly conduct for interfering with police as Toth was booked for a DUI.

“I clearly had one drink too many and I am deeply embarrassed about the things I said," she told Us in a statement at the time. "It was definitely a scary situation and I was frightened for my husband, but that is no excuse. I was disrespectful to the officer who was just doing his job. The words I used that night definitely do not reflect who I am. I have nothing but respect for the police and I'm very sorry for my behavior."

A source told Us at the time, "Ryan doesn't care what she does. It's about the kids.”

Toth was sentenced to community service, one year of probation and an alcohol education program after pleading guilty, while Witherspoon pleaded no contest to disorderly conduct and was ordered to pay a fine.

"I think more of the problem was age. When we got together, we were so young," Phillippe told Larry King about his divorce in March 2015. "I think it can create issues with two people in this industry because there's so much noise that goes along with it."

“I got married when I was 23 and I had two kids by the time I was 27. So I don’t know, you know, sometimes it’s good to know yourself,” Witherspoon admitted on ITV’s Lorraine show in 2017. "I would never change anything [but] I’ve said to my daughter, I think, you know, [at] 25, you start to know yourself a little bit better."

After Phillippe’s ex-girlfriend Elsie Hewitt accused him of assault, she called Witherspoon to testify in the 2019 trial. He vehemently denied the allegations at the time and settled the case before the trial was set to begin.

The exes made headlines in October 2020 for celebrating Deacon’s 17th birthday together.

During an interview on the "We Are Supported By" podcast, Witherspoon opened up about the difficulties she faced when she became a mother in 1999. “I did not have a lot of support with my first baby and I learned really early, like, this is not going to work,” the Little Fires Everywhere star recalled. “I tried to muscle through for five months with Ava, just not sleeping and I became delirious.”

She added that she probably wouldn't have been able to keep working even if she'd wanted to. “I was lucky enough to have money saved and I didn’t have to work, but it’s just not a one-person job,” the Hello Sunshine founder explained. “I would even say it’s not a two-person job.”

While celebrating Deacon’s 18th birthday, Phillippe noted that the twosome were “lucky” to be his parents.

The proud dad added: “I’d say we did pretty good @reesewitherspoon.”

A source told Us Weekly that their coparenting dynamic had “never been better” amid the coronavirus pandemic.

“Ryan has been an awesome parent … and everything pretty much stops for him when his kids need him,” the insider exclusively revealed. “Even during the pandemic when he’s been in literally another country, he’s present in their lives and he is still the ‘cool parent’ in their eyes. … He is really proud of who they’ve become.”

The exes have long been candid about which parent more closely resembles Ava and Deacon.

“What I get a lot lately is they think Deacon looks like her and Ava looks like me,” Phillippe later quipped to Extra in 2022. “My response is always, ‘Duh … How are you surprised that children look like their parents?’ Isn’t that biologically how it’s meant to work?”