Highlights
- Reese Witherspoon is avoiding dark roles and sticking to her "good girl" image after her divorce from Jim Toth.
- Fans have questioned her image after she dated Jake Gyllenhaal, her ex-husband Ryan Phillippe's friend.
- Despite their past, Reese and Ryan have maintained a co-parenting relationship and support their children's careers.
Recently, Reese Witherspoon said that she's avoiding dark roles following her divorce from Jim Toth. She explained that it's also not on-brand for her to take on heavier stories. However, fans have been questioning her "good girl" image after digging up her past actions after her divorce from her first husband Ryan Phillippe — with whom she shares two children, her doppelganger Ava and the very private Deacon.
After their split, Witherspoon dated Phillippe's friend, Jake Gyllenhaal. To some fans, it shows that the Legally Blonde actress also has her own red flags. At that time, her ex-husband was vocal about their breakup during interviews. He even commented on Witherspoon and Gyllenhaal's two-year affair.
Reese Witherspoon Dated Ryan Phillippe's "Old Workout Buddy" Jake Gyllenhaal
Witherspoon started dating Phillippe's "old workout buddy," Gyllenhaal in 2007 after working together on the film, Rendition. The former couple had just announced their divorce a year before. "We are saddened to announce that Reese and Ryan have decided to formally separate," said their formal statement back then. "They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time."
In October 2008, The Morning Show star appeared to be head over heels for Gyllenhaal. "He's very supportive," she told Vogue at that time. "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 Donnie Darko actor was also close to Ava and Deacon. "Jake is a great cook," Witherspoon shared to InStyle. "He does a lot. We spend the weekends outside L.A, in Ojai, where I have a farmhouse. We have chickens and we grow cucumbers and tomatoes. I love it."
Gyllenhaal "learned so much" from the kids, "and somehow they just become the center of your life and the way you look at things." He added that "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 two called it quits in 2009, with a source claiming that "Jake would marry [Reese] tomorrow, but Reese doesn't want to go there yet."
In 2010, a 29-year-old Jake Gyllenhaal dated Taylor Swift, 20, after his breakup with Reese Witherspoon — who married her second husband, Jim Toth in 2011.
Ryan Phillippe Supported Reese Witherspoon & Jake Gyllenhaal's Relationship
In 2008, Phillippe told Howard Stern that he approved of Witherspoon dating Gyllenhaal. "He's a good dude," said the Cruel Intentions alum. "I love her and I want her to be happy, and it seems like she is." A week later, he admitted to USA Today that it was "bizarre" seeing photos of the couple together.
"There's plenty of times when I say, 'What a strange situation I've found myself in,'" he explained. "But at a certain point you know it's going to happen, so you are prepared in some fashion." Back then, Phillippe was rumored to be dating Abbie Cornish, his Stop Loss co-star.
When asked if he could see himself getting married again — without confirming his relationship with Cornish — he said: "I can see getting married again. And I can certainly see possibly having children again. I'm pretty young, and there are many beautiful things about that idea of marriage and family."
He added that "it just doesn't always work out perfect for everybody. But I've done all I'm going to do in terms of talking about that part. It's fair to her and fair to myself to move on. At this point in time I feel in a pretty good place." There were rumors that the 54 star broke up with Witherspoon because he got intimidated by her success.
However, the two have always said in interviews that they simply got married at a young age. She was 23, he was 24. Here's a timeline of their relationship:
1997 | Reese Witherspoon and Ryan Phillippe met a birthday party |
1998 | They got engaged |
March 1999 | They starred in Cruel Intentions together |
June 1999 | They had their wedding in Charleston, South Carolina |
September 1999 | They welcomed baby no.1, Ava |
March 2002 | After Witherspoon insisted on announcing the Oscar winner during their co-presentation, Phillippe said: "You make more than I do, so go ahead." |
August 2002 | They started going to couples therapy |
October 2003 | They welcomed baby no.2, Deacon |
October 2006 | They announced their separation |
2008 | The divorce was finalized |
Reese Witherspoon & Ryan Phillippe Maintain A Co-Parenting Relationship
Phillippe later clarified in 2022 that he wasn't "jealous" of Witherspoon's fame when they were together. "People were always trying to pit us against each other, and any time there were rumblings that we were going through a rough patch, they would make it seem like it was because I was jealous," he told The Guardian.
"Man, I am so pro-woman," he added. "I have three sisters, I was raised by women, so I never felt that way. But that's the way people wanted to paint me. And that was unfortunate at times, but if people project a broad-brushstrokes image on to you, what can you do about it?" He also noted that he and the Big Little Lies star are "great co-parents."
"We did a good job as co-parents, and I knew that we would even back when we were very young," Phillippe reflected. "We met at her 21st birthday party, and then she was with child, but – knowing how volatile Hollywood relationships can be – I knew that even if we didn't make it, she would be a great person to raise kids with."
He went to say that he had "never said a bad word about her or our past, and I never would. I respect and admire her, and we made some pretty great and beautiful kids." In April 2023, he and Witherspoon reunited to support the release of their son's new album, A New Earth.
Ava Phillippe is currently modeling after graduating from UC Berkeley while Deacon Phillippe is presently pursuing music and studying at the New York University (NYU).
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