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Reese Witherspoon has been one of America’s Sweethearts since the early 1990s, when her breakout role in The Man in the Moon put her on the map. Since then, the Oscar-winning actress has been a staple in Hollywood for both acting and producing. And with being one of the biggest A-listers in Hollywood, it’s typical for people to want to know all the details about their life — especially in the dating department.

Over the years, Witherspoon has been linked to quite a few A-listers (and even married one!) Like quite a few stars in Hollywood, Witherspoon usually keeps her dating life on the more private side.

Many thought Witherspoon was out of the dating game once she tied the knot with her second husband Jim Toth. However, the pair broke their divorce news on Witherspoon’s Instagram in a joint statement, reading, “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.”

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

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It seems that the Legally Blonde star is single once again, and while this time is no doubt difficult for her, we know she’ll continue living her best life.

Check out all of the men Witherspoon has been married to, dated, or been linked to over the years below:

During a 2015 Reddit AMA, Jeremy Sisto revealed he and Reese Witherspoon had a relationship when they were teenagers in 1992 after meeting on the set of Desperate Choices: To Save My Child. “Reese was my first actress girlfriend. We had a long-distance relationship for a long time,” he said.

Sisto added that they split after a year when Witherspoon left to film in Africa, “I guess I thought she had broken up with me because she didn’t call that much. She’s a great person.”

So here’s the thing: even though Chris O’Donnell and Reese Witherspoon may have looked adorable at the American Museum of the Moving Image Salute to Al Pacino in 1993, but they were just friends. An insider told People per Hello back in 1993, “Chris really likes her, [but] they’re just friends.”

What could have been!

This one may be one of the most confusing ones. Did they date? Did they not date? Stephen Dorff and Reese Witherspoon were a big question mark for a while, but we have the answer.

Despite their on-screen matchup in S.F.W. and constant rumors, the two were never an item. In fact, Witherspoon said she “wouldn’t date Dorff for all the money in the world,” telling Details, “I really admire the girls who do hold Dorff’s attention. I don’t know if it’s because he doesn’t know what he wants, or that he knows exactly what he wants and if that person doesn’t apply, he’s going to find it somewhere else. You have to be comfortable giving him space. I’m not that kind of girl.”

After being linked together as an on-screen matchup in Fear, Mark Wahlberg and Reese Witherspoon were the center of dating rumors throughout the mid-1990s. However, neither have ever confirmed or denied the rumors.

Reese Witherspoon and Ryan Phillippe were the it-couple in the late 1990s and early 2000s. Now, despite many people believing they met on the set of the 1999 hit Cruel Intentions, they actually originally met when he crashed her 21st birthday party in 1997.

Reese told Jane magazine in 1998 about the first thing she said to him at her party, “I don’t know what came over me—maybe the seven Midori sours—but I told him, ‘I think you’re my birthday present.’ He thought it was so flattering, and now that I think about it…how embarrassing!”

The two dated for a couple of years before marrying in 1999 in South Carolina. Soon after, they welcomed their first child together, a daughter named Ava. They later welcomed a son named Deacon, in 2003.

However, after nearly seven years of marriage, the two separated in 2006. The pair finalized their divorce in 2007.

Phillippe told Larry King Now per InStyle that he believes the two split up due to the fact of how young they were when they first got together, “I think more of the problem was age. When we got together we were so young. I think it can create issues with two people in this industry because there’s so much noise that goes along with it.”

They continue to co-parent their two kids!

Truly a couple that everyone forgot about: Reese Witherspoon and Jake Gyllenhaal. The two originally met after co-starring in the 2007 thriller Rendition, and soon started dating.

In a previous interview with Vogue in 2008, she said, “He’s very supportive. Suffice it to say, I’m very happy in life, and I’m very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that’s all you can hope for in life. I am very blessed in that way.”

The couple split in 2009.

Soon after Reese Witherspoon broke up with Jake Gyllenhaal, she met her second husband Jim Toth, at a party, where he came to rescue her. In a 2012 interview with Elle, she recounted the story, saying, “it happened out of the blue.”

“This really drunk guy was hitting on me, making such an idiot of himself, yelling at me. He was, like, [slurring, scowling, pointing finger in her face] ‘You don’t know me.’ And I was like, ‘Yeah, I know. I don’t know you,'” she said. “Jim came over and said, ‘Please excuse my friend. He’s just broken up with someone.’ Jim was a really good friend, pulling him out of that situation. That’s just kind of who he is, a really good person.”

They got engaged that year in 2010, and in March 2011, they married in a backyard ceremony. Only a year later, they welcomed their son in 2012, named Tennessee.

They celebrated 11 years of marital bliss before shocking the world in March 2023 about their joint decision to divorce.