Reese Witherspoon’s Dating History: Ryan Phillippe, Jake Gyllenhaal, Jim Toth and More of Her A-List Romances

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Reese Witherspoon’s Dating History: Ryan Phillippe, Jake Gyllenhaal, Jim Toth and More of Her A-List Romances

What, like it’s hard? Reese Witherspoon has romanced multiple A-listers throughout her time in the spotlight, but not all of her relationships have had happily ever afters. After meeting Ryan Phillippe at her 21st birthday party in 1997, the twosome starred as love interests in 1999’s Cruel Intentions. The sexy flick may have made fans swoon over Witherspoon and Phillippe’s characters at the time, but the Big Little Lies star later told Andy Cohen that her and Phillippe’s children — Ava, born in 1999, and son Deacon, born in 2003 — had absolutely no desire to watch the movie. “They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she told the Bravo host in 2015. The Shooter alum, for his part, recalled going on a walk through Manhattan with Witherspoon and their children post-divorce. (The pair called it quits in 2006 after five years of marriage. They finalized their split in 2008.) “It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [here] … and [the kids] were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” he told Huffington Post Live at the time, noting that the former spouses were in a “really great place” at the moment. Still, the divorce took a toll on Witherspoon for some time. [jwplayer 4YCMU3VR-zhNYySv2] “I spent a few years just trying to feel better,” the Oscar winner recalled to 60 Minutes in 2014. “You know, you can’t really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn’t making things I was passionate about, I was just kinda working. It was really clear the audiences weren’t responding to anything I was putting out there.” However, she soon moved on with publicist Jim Toth, whom she wed in 2011. Witherspoon and Toth welcomed their son, Tennessee, the following year. With the exception of their highly-publicized arrest in 2013 — during which Toth was booked for a DUI and Witherspoon was handcuffed for disorderly conduct — the Wild actress and her husband enjoyed a low-key romance for more than a decade. In March 2023, however, the pair announced their split. “It is with a great deal of care and consideration that we have made the difficult decision to divorce,” the estranged couple shared via social media at the time. “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.” The exes 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.” Keep scrolling for Witherspoon’s dating history throughout the years:

Credit: Image Press Agency/NurPhoto/Shutterstock

Reese Witherspoon’s Dating History: Ryan Phillippe, Jake Gyllenhaal, Jim Toth and More of Her A-List Romances

What, like it’s hard? Reese Witherspoon has romanced multiple A-listers throughout her time in the spotlight, but not all of her relationships have had happily ever afters. After meeting Ryan Phillippe at her 21st birthday party in 1997, the twosome starred as love interests in 1999’s Cruel Intentions. The sexy flick may have made fans swoon over Witherspoon and Phillippe’s characters at the time, but the Big Little Lies star later told Andy Cohen that her and Phillippe’s children — Ava, born in 1999, and son Deacon, born in 2003 — had absolutely no desire to watch the movie. “They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she told the Bravo host in 2015. The Shooter alum, for his part, recalled going on a walk through Manhattan with Witherspoon and their children post-divorce. (The pair called it quits in 2006 after five years of marriage. They finalized their split in 2008.) “It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [here] … and [the kids] were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” he told Huffington Post Live at the time, noting that the former spouses were in a “really great place” at the moment. Still, the divorce took a toll on Witherspoon for some time. [jwplayer 4YCMU3VR-zhNYySv2] “I spent a few years just trying to feel better,” the Oscar winner recalled to 60 Minutes in 2014. “You know, you can’t really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn’t making things I was passionate about, I was just kinda working. It was really clear the audiences weren’t responding to anything I was putting out there.” However, she soon moved on with publicist Jim Toth, whom she wed in 2011. Witherspoon and Toth welcomed their son, Tennessee, the following year. With the exception of their highly-publicized arrest in 2013 — during which Toth was booked for a DUI and Witherspoon was handcuffed for disorderly conduct — the Wild actress and her husband enjoyed a low-key romance for more than a decade. In March 2023, however, the pair announced their split. “It is with a great deal of care and consideration that we have made the difficult decision to divorce,” the estranged couple shared via social media at the time. “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.” The exes 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.” Keep scrolling for Witherspoon’s dating history throughout the years:

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Jeremy Sisto

Before her romance with Phillippe, Witherspoon was one-half of another iconic ‘90s couple while dating Clueless star Sisto.

“[Reese] was my first actress girlfriend,” the Waitress actor recalled during a 2015 Reddit AMA, revealing the two hit it off while working on a 1992 TV movie. “We had a long-distance relationship for a long time,” he shared, gushing, “I was so into her.”

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Ryan Phillippe

Sparks flew when the I Know What You Did Last Summer star met Witherspoon at her 21st birthday party in 1997. The next few years were golden for the then-couple, who starred alongside each other in 1999's Cruel Intentions, got engaged — and married! — and welcomed their first-born, daughter Ava. Deacon joined the family four years later. Seven years after they wed, the pair split amid rumors that Phillippe was cheating on the Man in the Moon star with Abbie Cornish, whom he went on to date. (The Locksmith star denied the cheating allegations.)

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the actors 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.” They finalized their divorce in 2008. Despite their personal turmoil, Witherspoon and Phillippe remain dedicated coparents to their children.

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Jake Gyllenhaal

Witherspoon began dating Gyllenhaal in 2006 while working together on the movie Rendition. After the Election star ended their three-year relationship in 2009, a source exclusively told Us that there was nothing significant that caused their split. "No one cheated," a source told Us. "There was no drama."

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Jim Toth

One year after her split from Gyllenhaal, Witherspoon began dating Toth. Their relationship quickly progressed, tying the knot in 2011 and welcoming son Tennessee one year later.

In 2013, however, Witherspoon made headlines for her uncharacteristic behavior when she was arrested for disorderly conduct and Toth for a DUI. The actress asked the police officer if he knew her name, per the police report at the time.

“‘I answered, 'No, I don't need to know your name.' I then added, 'Right now,’” the officer recalled saying, per Variety. The document added that “Mrs. Witherspoon stated, 'You're about to find out who I am.'" The Your Place or Mine star later apologized for her behavior in a statement to Us.

“I clearly had one drink too many and I am deeply embarrassed about the things I said. 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."

Toth, who was driving the car, was sentenced to community service, one year of probation and an alcohol education program after pleading guilty. Witherspoon, for her part, pleaded no contest to disorderly conduct and was ordered to pay a fine.

While the couple’s only headlines throughout the next decade were sweet ones — many years of celebrating anniversaries and spending time with their son and Witherspoon’s elder children — Toth and Witherspoon announced the end of their marriage in March 2023.

“It is with a great deal of care and consideration that we have made the difficult decision to divorce,” they wrote via social media. “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.”

The former couple 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.”