Reese Wtherspoon Dating: A Complete Timeline of Her Relationships

By James Mercado On Mar 30, 2023

Since the early 1990s, when her breakthrough performance in The Man in the Moon made her famous, Reese Witherspoon has been regarded as one of America’s Sweethearts. Since then, as an actress and a producer, the Oscar-winning actress has been a mainstay in Hollywood.

And because they are among Hollywood’s most incredible A-listers, it is common for people to be curious about every aspect of their lives, particularly when it comes to dating.

Witherspoon has dated and been associated with several A-list celebrities throughout the years. Like many Hollywood celebrities, Witherspoon typically maintains her love life on the more secret side.

After marrying her second husband, Jim Toth, many people believed Witherspoon was no longer interested in dating.

“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 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 family as we navigate this next chapter. These matters are never easy and are highly personal. We truly appreciate everyone’s respect for our family’s privacy.

The Legally Blonde actress appears to be single once more, and while she will undoubtedly find it challenging at this time, we know she will continue living her best life.

See below for a list of every man Witherspoon has ever been married to, dated, or otherwise connected to:

Jeremy Sisto

Jeremy Sisto claimed he and Reese Witherspoon started dating while they were teenagers in 1992, after meeting on the set of Desperate Choices:

To Save My Child during a 2015 Reddit AMA. “My first actress girlfriend was Reese. He stated that we were in a long-distance relationship for a very long time.

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.”

Chris O’Donnell

But here’s the thing: Chris O’Donnell and Reese Witherspoon were pals even if they may have looked cute together in 1993 at the American Museum of the Moving Image Salute to Al Pacino. In 1993, a source reportedly told People through Hello, “Chris really likes her, [but] they’re just friends.”

What might’ve been!

Stephen Dorff

This one might be among the most perplexing. A date was there? They didn’t go on dates. Reese Witherspoon and Stephen Dorff were a big mystery, but now we know the solution.

Here, you can also look up dating articles for other celebrities:

Despite persistent rumors to the contrary and their on-screen romance in S.F.W., the two never got together. Witherspoon said she “wouldn’t date Dorff for all the money in the world,” telling Details, “I 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 knows exactly what he wants, and if that person doesn’t apply, he will find it somewhere else. You have to be comfortable giving him space. I’m not that kind of girl.”

Mark Wahlberg

Mark Wahlberg and Reese Witherspoon became the subject of dating rumors all during the mid-1990s after being mentioned as an on-screen couple in the film Fear. The rumors have never been confirmed or refuted by anyone, though.

Ryan Phillippe

In the late 1990s and early 2000s, Reese Witherspoon and Ryan Phillippe were the go-to couples. They first met when he crashed her 21st birthday party in 1997, even though many people still think they first connected on 1999 smash Cruel Intentions set.

Reese recalled to Jane magazine in 1998 that she informed him, “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!”

They dated for a few years before marrying in South Carolina in 1999. They soon had Ava, a daughter, as their first child together. In 2003, they welcomed a boy they named Deacon.

Unfortunately, the couple separated in 2006 after over seven years of marriage. In 2007, the couple divorced legally. According to InStyle, Phillippe told Larry King Now that he thinks the couple’s breakup was caused by how young they were when they initially started dating.

“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 raise their two children together!

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