For over 20 years, Reese Witherspoon has been a familiar face on our screens. From her iconic role in Legally Blonde to her recent starring role in the hit TV drama Big Little Lies, the actor has several classics under her belt.
But it was really her role in the 90s cult classic Cruel Intentions that first shone a spotlight on her.
The actor would eventually go on to settle down and have three children – with two belonging to her Cruel Intentions co-star, Ryan Phillippe.
The couple, who played Sebastian Valmont and Annette Hargrove in the film, proved they had more than on-screen chemistry and went on to marry shortly after.
Alas, as is the way with young Hollywood couples, the pair eventually went their separate ways, with Witherspoon pursuing relationships with other famous names in the industry.
Here’s a look back at the actress’ relationship history.
Ryan Phillippe
Witherspoon and Phillippe first met at the actress’ 21st birthday party in 1997.
“I don’t know what came over me — maybe the seven Midori sours — but I told him, ‘I think you’re my birthday present,’” she told Jane Magazine in 1998.
“He thought it was so flattering, and now that I think about it… how embarrassing!”
Young and in love, their relationship moved quickly and they ended up becoming engaged one year after they met.
But before they tied the knot, Witherspoon became pregnant with their first child, daughter Ava.
In 1999, three months after the premiere of cult classic Cruel Intentions, the couple married in an intimate ceremony in Charleston, South Carolina while Witherspoon was six months pregnant.
Three months later she gave birth to Ava and four more years after that they welcomed their son, Deacon.
Alas, after seven years of marriage the pair announced they were separating in 2006.
“We are saddened to announce that Reese and Ryan have decided to formally separate,” a representative for the couple 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.”
Nine years later, Phillippe told Larry King that their age was a big factor behind their divorce.
"I think more of the problem was age. When we got together we were so young," he said. “I think it can create issues with two people in this industry because there's so much noise that goes along with it."
Witherspoon echoed the same message in 2017 during an appearance on ITV’s Lorraine.
"I got married when I was 23 and I had two kids by the time I was 27. So I don’t know, you know, sometimes it’s good to know yourself," she said.
"I would never change anything," she continued, explaining, "I've said to my daughter, I think, you know, [at] 25, you start to know yourself a little bit better."
Despite their divorce, the actors have remained friends while continuing to co-parent their two kids.
"She’s happy and remarried and our kids are incredible. I’m proud of the way we handled it and who our little people are," told Phillippe HuffPost Live.
Jake Gyllenhaal
After her divorce, Witherspoon went on date Hollywood actor Jake Gyllenhaal. The pair met while filming the 2007 film Rendition, though they had no scenes together on-screen.
"He's very supportive," Witherspoon told Vogue in 2008. "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."
Throughout their two-year relationship, Gyllenhaal was often photographed with Witherspoon and her two kids.
"I've learned so much from the kids in my life, and somehow they just become the centre of your life and the way you look at things," Gyllenhaal told Grazia Australia at the time.
"Obviously I exist in my girlfriend's world and my sister's world in a different way, but it's opened my heart and I feel much more grown up and want to be grown up as a result of it."
Unfortunately, the pair ended up going their separate ways in 2009.
While little is known about why the actors split, rumours began floating around that Witherspoon didn't want to remarry.
"Obviously, I’m not far enough out of being married to think about doing it again," she told Parade in 2008. "You sort of reconstitute your family. You find a family with people who come into your life for a reason."
Meanwhile, a source reportedly told People "Jake would marry [Reese] tomorrow."
Regardless of why the split, Gyllenhaal spoke fondly about Witherspoon in 2016.
“She is, as I would say about most of the women who I’m close friends with or had relationships in my life, one of the smartest, strongest people I’ve ever met,” he said during The Jess Cagle Interview.
Jim Toth
Witherspoon and Toth met entirely by accident – the Hollywood agent ran into the actor in 2010 at a party when Toth's friend was drunkenly hitting on her.
"It happened out of the blue," Witherspoon recalled to Elle in 2012.
"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!'"
Jim ended up stepping in and saving her from the conversation.
"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," she told the publication.
From there, the couple wasted no time getting to know each other and reportedly began dating around January 2010.
Just under a year later, Toth proposed in December 2010.
The pair ended up tying the knot in 2011 at Witherspoon’s California Ranch and a year later they welcomed their son Tennessee, who is now seven.
"He’s an incredible man, a wonderful organiser, a great leader. He knows how to get people together," Witherspoon told People in 2016.
"He’s very patient and funny with the kids. And he really encourages them to see the humour in life."
Throughout their marriage, Witherspoon said her husband continuously supported her career and encouraged her to try new things.
Speaking with Harper’s Bazaar, she explained that he played an important role in helping her become a producer.
"He said, 'You should produce movies. You read more books than anybody I know. You should just buy some of them and turn them into films.'"
A few months after marrying Toth, the actor admitted he wouldn't have typically been her type.
"When I was 20, if you'd asked me ... I wouldn't have said Jim," she said.
"Jim's like, 'I'm gonna show you every day what a good partner is, what a good person is, I'm going to take care of you. I'm going to do it so much that you're gonna get used to it'. I was like, 'What are you talking about? I've never had anybody like that in my life'."
After almost 12 years together, the pair announced they are getting a divorce.
"We have some personal news to share," they wrote in a joint statement.
"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.
"Our biggest priority is our son and our entire family as we navigate this next chapter."
This article was published on May 31, 2020 and was updated with new information on March 25, 2023.
Feature Image: Getty.
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