What Jake Gyllenhaal's Exes Have Said About Him

Jake Gyllenhaal is known for his performances in a plethora of successful movies, such as 2005's "Brokeback Mountain" and 2014's "Nightcrawler." Due to his high profile as an Oscar-nominated actor, Gyllenhaal has also found himself in the news for more personal reasons, including who he has dated. Since 2018, the actor has been in a relationship with French model Jeanne Cadieu, although the couple has managed to keep much of their romance private. But in the past, some of Gyllenhaal's exes have been more outspoken about the "Nocturnal Animals" star.

During a 2015 interview with Howard Stern, Gyllenhaal got candid about his love life and his approach to relationships. "I believe in monogamy," he told the SiriusXM host. "I believe in when you meet someone who's right, it'll be right and you'll stay there." As for why he had yet to marry, the actor explained, "I think I probably just got scared."

Join us as we explore what all of Jake Gyllenhaal's exes have said about him so far.

At one time, Kirsten Dunst and Jake Gyllenhaal were one of Hollywood's golden couples. The pair was introduced by Jake's sister, Maggie Gyllenhaal, with whom Dunst starred in 2003's "Mona Lisa Smile." They started dating in September 2002, but Gyllenhaal's rep revealed they split in July 2004. As well as being a paparazzi favorite, Dunst got candid about her relationship with the "Donnie Darko" star on a number of occasions. 

Of her romance with Gyllenhaal, Dunst reportedly told MTV (via TheThings), "Jake was the love of my life. He was, is, and always will be ... He's a moron. And that's what I love about him." She also allegedly suggested that they were both very different people, which may have been why their relationship came to an end. "Jake and I couldn't last," she said in the same interview. "He's a stay-at-home boy, and I'm an out-of-town girl." 

In 2009, Dunst reflected on her former romance with the actor once again, telling Allure (via Us Weekly), "It would be nice to see him ... But we're not good friends." While their relationship didn't work out, it seems as though there are no hard feelings between Dunst and Gyllenhaal. And although they've since moved on, it appears that Dunst was extremely fond of Gyllenhaal when they dated.

Jake Gyllenhaal reportedly went on some dates with Oscar winner Natalie Portman in 2002 before briefly dating her again in 2006, via E! News. Portman and Gyllenhaal would later co-star in the 2009 movie "Brothers," along with Tobey Maguire. Portman and Gyllenhaal's chemistry in the film and during interviews led to rumors swirling regarding their relationship status. In 2009, Gyllenhaal even interviewed Portman for Interview magazine, in which the "Black Swan" star said of her former partner, "You're a very peaceful man, Jake." She also dished, "I mean, you're a really good cook, you know how to build things — you can make things with your hands."

When Gyllenhaal was honored as one of People's "leading men" in their Sexiest Man Alive issue in 2009, Portman said of her ex (via Just Jared), "Jake is the kind of guy who can do a spot-on impression of someone you work with that will make you giggle. He plays guitar and has a great voice. Kids and dogs love him. He loves his mom and sister and girlfriend. He's perfect." She also joked, "Too bad he's ugly." Clearly, Gyllenhaal and Portman have a lot of love for one another, and seemingly remain close friends even though their romantic relationship didn't turn into anything serious.

Jake Gyllenhaal co-starred with Reese Witherspoon in 2007's "Rendition," and during a reshoot for the movie in Los Angeles in 2006, the pair reportedly hit it off, according to one of People's sources. However, the couple's romance was far from simple, especially as Witherspoon had only recently split from her former husband, Ryan Phillippe. As a result, Witherspoon and Gyllenhaal reportedly broke up briefly in June 2007 before being spotted together in Rome in October 2007. After two more years together, Witherspoon allegedly called off their relationship for good in November 2009.

While their romance didn't go the distance, Witherspoon spoke highly of Gyllenhaal while they were together. In October 2009, she opened up to InStyle (via Marie Claire), saying, "Jake and I went to Coachella this year." She also gushed about their quiet life, which involved retreating to a farmhouse in Ojai, California, on the weekends. "We have chickens and we grow cucumbers and tomatoes," she told InStyle. "Jake's a great cook, he does a lot." 

In March 2009, the "Legally Blonde" star sang Gyllenhaal's praises again, telling Elle (via NBC Washington), "He really is a fantastic guy." Unfortunately, though, Gyllenhaal and Witherspoon's relationship just wasn't meant to be. It was also rumored that Witherspoon simply wasn't ready to commit to another long-term relationship following her divorce from Phillippe. In November 2008, she explained to Parade, "Obviously, I'm not far enough out of being married to think about doing it again." 

Jake Gyllenhaal was thrown into the spotlight in a major way in 2021 when Taylor Swift released her album "Red (Taylor's Version)," including a ten-minute version of her song "All Too Well," which famously explores the singer's short-lived relationship with the actor. Swift was first linked to Gyllenhaal in October 2010, when the pair spent time backstage at "Saturday Night Live." In November 2010, they were photographed enjoying maple lattes in Brooklyn before spending Thanksgiving together. Sadly, it was all over by December 2010, with reports suggesting that the pair spent the holidays apart.

In January 2012, Swift seemingly reflected on the split in an interview with Vogue while discussing the inspiration behind her album "Red," which would be released in October 2012. "There's just been this earth-shattering, not recent, but absolute crash-and-burn heartbreak," she told Vogue, "and that will turn out to be what the next album is about. The only way that I can feel better about myself — pull myself out of that awful pain of losing someone — is writing songs about it to get some sort of clarity."

The lyrics featured in Swift's "All Too Well" hinted at discord in her former relationship with Gyllenhaal. Seemingly referencing their tense breakup, Swift sang, via Genius, "And you call me up again just to break me like a promise/So casually cruel in the name of being honest." But she also sang of her seeming appreciation of him, singing, "Oh, your sweet disposition and my wide-eyed gaze."

Anna Kendrick and Jake Gyllenhaal co-starred in 2012's "End of Watch" together, in which they played husband and wife. While it's unclear whether Kendrick and Gyllenhaal actually dated, rumors started circulating about the co-stars, and Kendrick's comments about the actor only stoked those fires. Discussing her time on set with Gyllenhaal, Kendrick told E! News, "It felt incredibly intimate. You're in character all the time because you're shooting all the time. So Jake and I would be holding hands and suddenly we'd be like, 'Oh, we're not filming.'" When questioned about whether she had to film any intimate scenes with Gyllenhaal, Kendrick seemingly got embarrassed, telling E! News, "Oh, my goodness — I'm actually blushing ... Yeah, it gets all sexy time with us."

During an interview with Extra, Kendrick also reflected on what it was like kissing Gyllenhaal onscreen. "He is a great kisser," she explained. "He's a real gentleman." While speaking with PopSugar, Kendrick sang her co-star's praises, saying, "Jake has such a commitment to getting people to open up." She also told the outlet that she got to rehearse a fake first date opposite Gyllenhaal to help them both prepare for playing a married couple. Whether or not the pair really dated in real life, it's clear that they spent a lot of time pretending to be a couple, which doesn't sound like a bad thing.

From December 16, 2014, until January 13, 2015, Jake Gyllenhaal starred opposite Ruth Wilson in the play "Constellations" on Broadway. During an interview with Net-a-Porter's The Edit (via E! News), Wilson addressed rumors that she was dating Gyllenhaal following their time together onstage. "He's adorable, a really good guy," she told the outlet. Seemingly distancing herself from romance rumors, Wilson also said, "We've become like brother and sister a little bit." She continued, "We spend so much time together. We trust that even if we have a little [disagreement] — which is going to happen because we're in a tense environment that demands a lot from us — we'll make up and we'll be fine. I trust him implicitly."

Rumors that Gyllenhaal and Wilson were dating started when the pair were reportedly seen kissing while out to dinner in December 2014. By May 2015, the romance rumors amped up when Gyllenhaal and Wilson were allegedly spotted kissing after attending a workout class together in New York City, per E! News. However, a love connection was never confirmed, so it's unknown if Gyllenhaal and Wilson actually dated or if they were just really, really good friends.