5 Men Reese Witherspoon Dated

Jeremy Sisto

During a Reddit AMA in 2015, the former Clueless star revealed that he had a brief romance with the Oscar-winning actress back in 1992, after meeting on the set of Desperate Choices: To Save My Child.

“[Witherspoon] was my first actress girlfriend,” Sisto said. “We had a long-distance relationship for a long time.”

The movie was filmed when Witherspoon was around 16 and Sisto was around 17 years old. In the film, Witherspoon played a teenager dying from leukemia.

“I was so into her,” Sisto continued. However, when Witherspoon took off for Africa to film 1993’s A Far Off Place, Sisto said he assumed the relationship was over.

“I guess I thought she had broken up with me because she didn’t call that much,” he admitted. “So, I moved on and met my ex-wife Marisa [Ryan]. When [Witherspoon] returned I found out that wasn’t her intention, but I had already gotten involved. Felt badly. She’s a great person.”

Chris O’Donnell

At 16, an up-and-coming Reese Witherspoon generated buzz after accompanying Chris O’Donnell to a tribute party for his Scent of a Woman costar Al Pacino in February 1993.

Though the actress flew to New York from her native Nashville to attend the soiree with the 22-year-old actor, the pair kept mum about their relationship, with the actor’s rep telling PEOPLE, “Chris really likes her, [but] they’re just friends.”

Ryan Phillippe

Once Hollywood’s golden couple, Witherspoon and Phillippe first met at the actress’ 21st birthday party before working together on the set of Cruel Intentions. In June 1999, they tied the knot in Charleston, South Carolina at the Old Wide Awake Plantation along the Stono River. At the time, Witherspoon was several months pregnant with their daughter, Ava.

During the course of their marriage, they welcomed two children together: their daughter Ava in 1999 and their son Deacon in 2003.

In October 2006, they announced they were splitting up in a joint statement. “We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the couple said. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.”

Not long after his marriage ended, Phillippe revealed in an interview with W magazine that the divorce 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,” he said. “It was the worst time of my life.”

Following their divorce, they have continued to co-parent their children, most recently celebrating Deacon’s high school graduation together in June 2022.

Jake Gyllenhaal

Picking up the pieces, Witherspoon moved on with actor Jake Gyllenhaal, her costar in the 2007 CIA thriller Rendition.

“He’s very supportive,” the actress said of her then-boyfriend, with whom she spent low-key weekends at her Ojai, Calif., farmhouse.

But after two years together, they split in November 2009. “Jake would marry [Reese] tomorrow, but Reese doesn’t want to go there yet,” a friend of the pair told PEOPLE.

Jim Toth

After a year-long, whirlwind romance with Hollywood agent Jim Toth, the couple got married in a backyard ceremony at her Ojai, Calif., ranch.

Speaking with Marie Claire in 2011, Witherspoon called herself “very lucky” to find her perfect fit in Toth. “Now I feel a great sense of relief and an incredible amount of support from my husband. … Somebody close to me once said, ‘Oh, no man will ever accept your children.’ And I just thought it was the most horrifying thing someone has ever said to me in my entire life. I was determined to find somebody who would make that not true. And I got lucky. I did. I got very lucky, and he’s wonderful. And so wonderful with the children. I’m very blessed.”

In March 2012, the couple announced they were expecting their first child together and that September they welcomed a son named Tennessee.

After more than a decade of marriage, the couple announced they were getting divorced on March 24, 2023, just a few days before their 12-year wedding anniversary.

“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,” they said. “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.”

“Our biggest priority is our son and our entire family as we navigate this next chapter,” they added. “These matters are never easy and are extremely personal. We truly appreciate everyone’s respect for our family’s privacy at this time.”