Jake Gyllenhaal Has More Celebrity Exes Than Just Taylor Swift

Jake Gyllenhaal’s first public relationship was with singer Jenny Lewis. According to Us Weekly, the two dated in 2001, just as Gyllenhaal’s acting career began taking off. When they dated, Lewis was the lead singer of the indie rock band Rilo Kiley. It’s unknown when Gyllenhaal and Lewis officially broke up, but the two did keep in touch after their split. He brought Lewis as his date to the 2011 Golden Globes, though just as friends. At the time, Gyllenhaal was nominated for best actor in a musical or comedy for his role as Jamie Randall in “Love & Other Drugs.”

Gyllenhaal started dating Kirsten Dunst in 2002. The two met through Gyllenhaal’s sister, actress Maggie Gyllenhaal, who worked with Dunst on the 2003 film “Mona Lisa Smile.” Their relationship developed fast, and shortly after they started dating, the couple reportedly moved into Dunst’s $1.7 million Los Angeles home and adopted a German shepherd, according to Variety.

The couple became notorious for their very intimate, public displays of affection after Dunst reportedly told News of the World that the two “spiced things up in the bedroom” and “had sex in cars, in the bathroom, and even by the sea” (via InStyle). Unfortunately, as happy as the couple seemed on various red carpets and public outings, like many relationships in your early 20s, their relationship eventually ended in July 2004.

Gyllenhaal’s rep broke the news to People in a statement, saying, “Kirsten and Jake remain the best of friends . . . Details regarding when and why their romantic relationship stopped are not being provided, but suffice it to say it happened some time ago. They are still very close.”

The exes didn’t remain very close, however. In a 2009 interview with Allure (via Us Weekly), Dunst told the publication, “It would be nice to see him . . . But we’re not good friends.”

Gyllenhaal briefly dated actress Natalie Portman in 2006. While introducing Portman at the 2011 Palm Springs Film Festival, Gyllenhaal revealed he met the actress at a Star Wars convention when he approached her to sign his Queen Amidala doll.

According to E! News, the two were initially romantically linked back in 2002 but didn’t make headlines until 2006, when they were spotted out on a date. It’s unknown how long their romance lasted, but it was brief.

Despite their romance fizzling out, the two remained friends over the years and worked together on the 2009 film “Brothers.” Gyllenhaal joked in his 2011 Palm Springs Film Festival speech that Portman’s veganism made dating difficult, saying, “It does get hard when you’re out to dinner with her.”

Gyllenhaal’s next long-term relationship was with actress Reese Witherspoon. According to People, the two were already acquaintances, as Gyllenhaal used to work out with Witherspoon’s ex-husband, Ryan Phillippe. However, their relationship heated up while filming the 2007 film “Rendition,” with a source close to the actress telling People, “Jake went and reintroduced himself to Reese . . . Things slowly progressed, but it was never something she thought would happen from the start. She just kind of developed this little crush over time.”

In October 2008, Witherspoon talked about her new boyfriend in an interview with Vogue (via E! News), saying, “He’s very supportive . . . 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 that’s all you can hope for in life.”

Gyllenhaal and Witherspoon were regularly spotted together throughout their relationship and often as a family with her kids. The pair continued dating until their split in November 2009. According to People, their breakup was partially because Gyllenhaal wanted to get married, while Witherspoon was more apprehensive about tying the knot after her divorce from Phillippe. A source told the publication, “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 . . . ”

Despite reportedly being dumped by Witherspoon, Gyllenhaal has spoken highly of her since their split, telling Entertainment Weekly in 2016, “She is . . . one of the smartest, strongest people I’ve ever met.”

Gyllenhaal and Swift sparked dating rumours after attending “Saturday Night Live” together in October 2010 after reportedly meeting through actress Gwyneth Paltrow at a dinner that year. In November 2010, the two were spotted walking together in Brooklyn while smiling and embracing. They even spent the Thanksgiving holiday with Gyllenhaal’s sister, Maggie Gyllenhaal.

The couple’s relationship was short-lived, however. By December 2010, the two went their separate ways. Regarding their breakup, a source told Us Weekly, “Jake just told her it wasn’t working out. Taylor is really upset and hurt. She feels really burned by him.”

Two years later, Swift alluded to their relationship in her 2012 song “All Too Well.” At one point in the song, Swift sings, “I left my scarf there at your sister’s house / And you’ve still got it in your drawer even now.” She continues, “But you keep my old scarf from that very first week / ‘Cause it reminds you of innocence / And it smells like me.” The infamous scarf Swift is referring to is believed to be the one she was pictured in while strolling with Gyllenhaal back in November 2010 while they spent Thanksgiving with Maggie.

Swift rereleased “All Too Well” in 2021 as part of her rerecorded album “Red (Taylor’s Version)” and further detailed their three-month-long relationship. In the 10-minute version of the song, she sings, “They say all’s well that ends well / But I’m in a new hell every time you double-cross my mind / You said if we had been closer in age maybe it would have been fine / And that made me want to die.”

Gyllenhaal started dating Sports Illustrated model Alyssa Miller in the summer of 2013 after the two met at a gym in New York City, according to E! News. They dated for six months before ultimately splitting in January 2014. A source told Us Weekly at the time that Gyllenhaal’s busy shooting schedule contributed to their split. “Things were really good between Jake and Alyssa right up until he had to leave for L.A. to go shoot a movie [‘Nightcrawler’] in the fall . . . Then the distance just really got to them,” the source said.

In December 2018, Gyllenhaal was officially linked with French model Jeanne Cadieu. The two travelled together in London and Greece that summer but weren’t confirmed as a couple until months later.

Cadieu is Gyllenhaal’s longest relationship, and the two remain mainly private about their personal and romantic life. The pair have been spotted in public a handful of times since they started dating, most recently at The New York Film Festival’s premiere for “The Lost Daughter” in September 2021, which Maggie Gyllenhaal directed.

Gyllenhaal seldom speaks about his relationship with Cadieu, but the actor did briefly touch on his girlfriend in an interview with Esquire in February 2022, saying, “In a lot of ways, we’re family . . . I’m in a relationship that is full of love and support. I feel so at ease.”