Both are Hollywood A-listers whose high-profile relationships have taken up a lot of bandwidth over the years, so perhaps it was inevitable that one day Reese Witherspoon and Jake Gyllenhaal would get together. While the romance turned out just to be a pitstop for both of them en route to longer lasting love, it was a pretty big deal at the time. Let’s cast our minds back …
How It Began
In 2006, Witherspoon was turning 30 and newly separated from Ryan Phillippe after seven years of marriage. She flew to Morocco to shoot political thriller Rendition and hit it off with costar Gyllenhaal, five years her junior. Nothing happened between the pair straight away, but People later reported that Witherspoon “just kind of developed this little crush over time.” Well, didn’t we all?
When they met again in Los Angeles a few months later to do reshoots, Witherspoon’s divorce was further down the line and she felt ready to date. In 2007, she told Ellen DeGeneres that she and Gyllenhaal were friends — but it did sound like a little more could be going on. “I have known Jake for years through different friends and he is just wonderful,” she said. “He’s very kind, generous and funny. Yeah, he’s great and I look forward to maybe making another film with him.” Sure enough, the pair were soon spotted together, clearly making more than just movies.
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How Long It Lasted
This was no rebound fling — the couple stayed together for well over two years, with Gyllenhaal bonding with Witherspoon’s children, Ava and Deacon. The actors enjoyed time together at Coachella and around the world on various movie sets.
How It Ended
Around Thanksgiving 2009, rumors emerged that the couple were splitting. While their reps initially insisted “they’re still together,” it soon became clear that they, well, weren’t. According to insiders, Witherspoon ended the relationship. “She felt pressured to wed again, but she wasn’t ready,” one source told Us Weekly. “She couldn’t give Jake enough and she got cold feet. Jake wanted all of her. It broke his heart.”
Another source told People: “Jake would marry her tomorrow, but Reese doesn’t want to go there yet, even though he would like to.”
Per the insider, “It’s totally and completely over. Reese was the one who had to do it. She just got out of a divorce and was so concerned with her family, she just didn’t have the time for him and he really demanded that.”
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In 2009, Witherspoon told Elle that her divorce from Phillippe had been “very humiliating and very isolating,” so perhaps it’s not surprising that she wasn’t ready to throw herself in headfirst again. Around the same time, she also told Parade that she wasn’t sure she would ever remarry. “Family is all we have in life, but I don’t know how I feel about marriage,” she said. “Obviously, I’m not far enough out of being married to think about doing it again. You sort of reconstitute your family. You find a family with people who come into your life for a reason.”
Interestingly, Witherspoon has also admitted that she likes to be in control in her relationships. “[My dad and uncle] taught me that in every relationship, the person least interested in maintaining it is going to dominate it, because they’ll never compromise,” she told Elle. “So you have to always maintain that position of least interest, and you’ll always control the relationship.”
What They Said About Each Other
During their relationship, these two were refreshingly open about how well it was going.
“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.”
The following year, she gave a little more insight into her cute, low-key life with Gyllenhaal. “Jake is a great cook, he does a lot,” she told InStyle. “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. It reminds me of where I grew up in Tennessee.”
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Meanwhile, Gyllenhaal talked to Grazia Australia about how much he loved spending time with Witherspoon’s kids. “I’ve learned so much from the kids in my life, and somehow they just become the center of your life and the way you look at things,” he said. “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.”
What They Say Now
Despite the narrative that Witherspoon had broken Gyllenhaal’s heart, he’s always been kind about her in subsequent interviews. “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 on The Jess Cagle Interview in 2016, 10 years after their first introduction.
Key Relationship Takeaways
Since their relationship, Gyllenhaal has mainly dated younger women — and looking back on what went down between him and Witherspoon, an older woman and divorced mom, it could be a conscious choice. After his infamous 2010 fling with Taylor Swift, he played the field before seemingly settling down in 2018 with his long-term love, Jeanne Cadieu, who is more than 15 years younger than him.
In 2021, he told The Howard Stern Show that “all I want is to be a good husband and father,” but he’s yet to fulfil his dream.
Witherspoon, meanwhile, did find another husband after all — she was married to Jim Toth from 2011 and 2023, with the ex-couple now coparenting son Tennessee.
So while Witherspoon and Gyllenhaal looked great together and clearly had fun along the way, ultimately they were two strong personalities in very different places.
