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

Credit: Frazer Harrison/Getty Images

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. The exes met in 1997 prior to filming 1999’s Cruel Intentions together, in which Phillippe played Sebastian Valmont, a wealthy prep school heartbreaker whose worldview is challenged when he unexpectedly falls for his conquest, Annette Hargrove (Witherspoon). Witherspoon and Phillippe tied the knot in June 1999 and welcomed their daughter, Ava, that September. Three years after welcoming son Deacon in October 2003, Witherspoon and Phillippe announced their split. At the time, 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. The pair announced their divorce in March 2023. Scroll down for a look back at Witherspoon and Phillippe’s ups and downs:

Credit: Frazer Harrison/Getty Images

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. The exes met in 1997 prior to filming 1999’s Cruel Intentions together, in which Phillippe played Sebastian Valmont, a wealthy prep school heartbreaker whose worldview is challenged when he unexpectedly falls for his conquest, Annette Hargrove (Witherspoon). Witherspoon and Phillippe tied the knot in June 1999 and welcomed their daughter, Ava, that September. Three years after welcoming son Deacon in October 2003, Witherspoon and Phillippe announced their split. At the time, 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. The pair announced their divorce in March 2023. Scroll down for a look back at Witherspoon and Phillippe’s ups and downs:

Credit: Bei/Shutterstock

March 1997

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!"

Credit: Moviestore/Shutterstock

March 1999

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

Credit: Bei/Shutterstock

June 1999

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

Credit: Broadimage/Shutterstock

September 1999

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

Credit: Peter Brooker/Shutterstock

March 2002

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.”

Credit: Richard Young/Shutterstock

October 2003

The duo welcomed son Deacon in October 2003.

Credit: Jim Smeal/BEI/Shutterstock

March 2006

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.”

Credit: Jim Smeal/BEI/Shutterstock

October 2006

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.

Credit: Henry Lamb/BEI/Shutterstock

October 2007

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.

Credit: Matt Baron/BEI/Shutterstock

2010

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.

Credit: Michael Buckner/Variety/Shutterstock

March 2011

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.

Credit: Steve Eichner/WWD/Shutterstock

April 2013

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.

Credit: Kristina Bumphrey/StarPix/Shutterstock; Jason Szenes/EPA-EFE/Shutterstock

March 2015

"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."

Credit: Gregory Pace/Shutterstock

September 2017

“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."

Credit: Alex Berliner/BEI/Shutterstock

2019

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.

Credit: Courtesy of Ryan Phillippe/Instagram

October 2020

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

Credit: Jordan Strauss/Invision/AP/Shutterstock

August 2021

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.”

Credit: Courtesy of Ryan Phillippe/Instagram

October 2021

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.”

Credit: Shutterstock (2)

December 2021

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.”

Credit: Courtesy of Ryan Phillippe/Instagram

October 2022

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?”

Credit: Christopher Polk/Getty Images for The Critics' Choice Awards

March 2023

Witherspoon announced her split from Toth after 11 years of marriage.

“We have some personal news to share … It is with a great deal of care and consideration that we have made the difficult decision to divorce,” the former couple, who share son Tennessee, said in a joint statement on March 24. “We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together.”

Credit: Getty Images (2)

April 2026

A source exclusively told Us that Witherspoon “is very close to Ryan” two decades after their divorce. “They have been coparenting through the years, and they are friends,” the insider said.

“Since her divorce from Ryan, she has been supportive of her kids going into the entertainment industry,” the source added. “Anything they want to do, they are both supportive.”

Credit: Courtesy of Ryan Phillippe/Instagram

May 2026

Witherspoon and Phillippe reunited on May 15 in New York City to watch their son, Deacon, graduate from New York University. The exes were photographed standing side by side and taking pictures of Deacon after he received his diploma. In snapshots obtained by People, Witherspoon and Phillippe also posed for solo pics with the graduate.

Phillippe later shared an Instagram Story photo of Deacon in the Big Apple after he received a degree in music. “The Graduate,” he captioned the snap, tagging his son.

The exes’ daughter, Ava, was also on hand for the special day as was Witherspoon’s youngest child, Tennessee.