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Reese Witherspoon: An in-depth look inside the actress’ dating history

From Ryan Phillipe to Jim Toth, a look back at her exes

reese witherspoon red© Photo: Getty Images
Faye James
Senior Editor
March 29, 2023
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Award-winning actress Reese Witherspoon has had her fair share of high-profile relationships. 

From her marriage to Ryan Phillippe to her most recent split from husband Jim Toth after almost 12 years, here's a more in-depth look at her dating history. 

Reese Witherspoon radiates in pretty floral dress

Jeremy Sisto

During a 2015 Reddit AMA, former Clueless star Jeremy Sisto revealed a brief romance with Witherspoon back in 1992 after meeting on the set of Desperate Choices: To Save My Child. Jeremy fondly remembered, "Reese was my first actress girlfriend. We had a long-distance relationship for a long time." However, when Reese left for Africa to film A Far Off Place, the relationship ended. Jeremy added, "I guess I thought she had broken up with me because she didn't call that much. She's a great person."

Chris O'Donnell

The then 16-year-old Witherspoon attended a tribute party for Al Pacino in February 1993 with Chris O'Donnell. Although they kept mum about their relationship, Chris’ rep told People at the time, "Chris really likes her, [but] they're just friends."

SEE: Reese Witherspoon shares wedding photo to mark her tenth anniversary

MORE: Reese Witherspoon's son Deacon spends time apart from famous mom amid Jim Toth split news

Ryan Phillippe

Hollywood's golden couple first met at Witherspoon's 21st birthday party and later worked together on Cruel Intentions.

They married in June 1999, and during their marriage, they had two children, Ava and Deacon.

The couple announced their separation in October 2006. Reflecting on the divorce in an interview with W magazine, Ryan said, "It was the darkest, saddest place I've ever been. There were a good four or five months of not being able to get out of bed. It was the worst time of my life."

Despite the challenges, the couple has continued to co-parent their children, most recently celebrating Deacon's high school graduation together in June 2022.

Jake Gyllenhaal

Reese moved on with actor Jake Gyllenhaal after working together on the 2007 film Rendition. 

The actress praised her then-boyfriend in an interview, saying, "He's very supportive." Despite a supportive two-year relationship, they split in November 2009. 

READ: Reese Witherspoon's daughter Ava makes statement about gender with powerful message

Jim Toth

In 2011, Reese married Hollywood agent Jim Toth after a whirlwind romance. She described herself as "very lucky" to find her perfect fit in a Marie Claire interview.

"Now I feel a great sense of relief and an incredible amount of support from my husband," she said. The couple welcomed their son, Tennessee, in September 2012.

On March 24, 2023, they announced their decision to divorce, emphasizing their priority to maintain their family's well-being during the transition.

In a joint statement, they said, "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.

“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."

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