Inside Jake Gyllenhaal's Relationship History

Jake Gyllenhaal loves love. At least, that's what the "Love and Other Drugs" actor told Howard Stern, confessing in 2015, "I love love, man. Yeah, are you kidding me?" Stern asked the actor how many times he'd been in love in his life, and he admitted, "Three times. Twice, maybe."

It's unclear exactly which past partners Gyllenhaal was referring to; despite prompting from Stern's co-host Robin Quivers, he declined to name names. The "Brokeback Mountain" star has been in numerous public relationships and had a fair few rumored flings, both with musicians and actors at his level of fame and with women far more obscure than he is. "There are a lot of beautiful women," he confessed. "There are opportunities. But I think at the same time, like... you find the right person? I believe in monogamy... I believe when you meet somebody who's right, it'll be right."

Read on for a look into Jake Gyllenhaal's relationship history, and, like a Swiftie getting their hands on new album's landing page for the first time, see if you can piece together the clues for which relationships he considers actual love and which were just "opportunities." 

Jake Gyllenhaal and his first famous girlfriend stayed pals

Jake Gyllenhaal was an up-and-coming actor best-known for starring in the 1999 space drama "October Sky" when he got into his first high-profile relationship with a fellow public figure. Gyllenhaal romanced Jenny Lewis, the lead singer of indie rock band Rilo Kiley, in 2001. He even brought her as his date to the premiere of "Donnie Darko," the film that would catapult Gyllenhaal to bona fide stardom. They broke up sometime shortly thereafter, but evidently remained close. Lewis would crop up again throughout Gyllenhaal's dating life, including when he took his later girlfriend Reese Witherspoon to watch her perform at Coachella.

Next, as People reported at the time, the former flames attended the Golden Globes together in 2011, causing widespread speculation about the status of their relationship. The Golden Globes date was shortly after Gyllenhaal's much-publicized breakup with Taylor Swift, sparking whispers that they were back together. When Swift released "We Are Never Ever Getting Back Together," Swifties wondered if the lyric "You would hide away and find your peace of mind / With some indie record that's much cooler than mine" was a reference to Lewis.

In 2020, Lewis clarified in a since-deleted tweet that she was already in a relationship when she went with Gyllenhaal to the awards show. "jake asked me to be his friend date for the @goldenglobes," she wrote, adding that the "Nightcrawler" star had asked her then-boyfriend for "permission."

Kirsten Dunst and Jake Gyllenhaal kept it interesting

Jake Gyllenhaal played one of Spider-Man's nemeses in "Spider-Man: Far From Home," but in 2002, he stole Spidey's girlfriend. Jake was introduced to Kirsten Dunst, who played Mary-Jane in Sam Raimi's trilogy, when his sister Maggie Gyllenhaal worked with her on "Mona Lisa Smile." They dated for two years.

Their longest-lasting impact on pop culture came when they visited a café in London, according to E! News. In memorable paparazzi photos that regularly go viral still, Jake looked on in consternation as Dunst ate a salad with her fingers. The "Bubble Boy" actor later told People that the paparazzi were annoying, but that they had little effect on their relationship. "Kirsten and I know what's real and what's not," he said. "We know what happens when you are both actors." The following month, though, a rep confirmed to the magazine that they had split "some time ago." Dunst later explained the reason behind the breakup to DigitalSpy, reasoning, "He's a stay-at-home boy and I'm an out-on-the-town girl." She also admitted that they had tried "risqué sex" to keep the relationship exciting, getting it on together on beaches and in cars. Witnesses even told the Daily Star (via SFGate) that the two had hooked up in a fitting room in a posh London shop. 

Alas, they eventually ended up going their separate ways. "If I saw him, it'd be nice to see him, but we're not good friends," Dunst confessed to Allure in 2009.

Jake Gyllenhaal moved in with Reese Witherspoon

After Kirsten Dunst, Jake Gyllenhaal moved on with another A-lister at the top of her '00s fame: Reese Witherspoon. According to People, the actors had known one another for years, as Gyllenhaal was reportedly a "workout buddy" of Witherspoon's ex-husband Ryan Phillippe, but it wasn't until reshoots on their movie "Rendition" that the two got closer. "Things slowly progressed, but it was never something she thought would happen from the start," a source told the outlet in early 2007. "She just kind of developed this little crush over time."

In 2008, Witherspoon opened up about her relationship to Vogue after being pressed for details. "He's very supportive," she allowed. "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."

Gyllenhaal moved in with her in 2008. They attended Coachella together and accompanied one another to various red carpets, with Gyllenhaal even reportedly growing close to her children. However, they split the following year. A source told Us Weekly that Gyllenhaal was ready to settle down, but apparently, Witherspoon's divorce was still too fresh for her to be able to commit. "She felt pressured to wed again but she wasn't ready," the source said. "She couldn't give Jake enough and she got cold feet. Jake wanted all of her."

Jake Gyllenhaal knew Taylor Swift all too well

As Swifties know all too well, Jake Gyllenhaal was next linked to Taylor Swift. They dated for about three months, and the relationship — according to the hints fans pieced together from Swift's album "Red" — was evidently a tumultuous one. They first sparked speculation after attending "SNL" and getting brunch together in October 2010, according to People. A source told the outlet, "It was hard to tell if they were together, but everyone was shocked that she brought him." Gwyneth Paltrow reportedly set them up, though the "Spider-Man: Homecoming" star was surprised anyone knew. "It's so weird. I wonder how people find out these things," she told USA Today. "It was a while ago."

Jake and Swift famously spent Thanksgiving at his sister Maggie Gyllenhaal's house, according to the Daily Mail. Swift would go on to reference the date in her music, infamously claiming Jake kept the scarf she accidentally left behind. They split by January. "He... said he could feel the age difference," a source dished to Us Weekly. "Taylor is really upset."

A decade later, after Swift's ten-minute version of "All Too Well" and its accompanying short film painted him out to have been a bad boyfriend, Jake spoke about the song for the first time publicly. "It has nothing to do with me," he insisted to Esquire. "It's about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that."

He had a lot of rumored flings with co-stars

After Taylor Swift, Jake Gyllenhaal was rumored to have dated a string of co-stars. None of the following relationships were ever confirmed, merely hinted at through body language experts, unnamed sources, and suggestive paparazzi shots... basically gospel, in other words. 

In 2012's "End of Watch," Gyllenhaal and Anna Kendrick played husband and wife. It seemed that their relationship off-screen may have been influenced by their on-screen chemistry; according to PopSugar, the actors were spotted cuddled up during a lunch break from filming. Fast-forward to the 2015 Spike TV's Guys Choice Awards where his "Southpaw" co-star Rachel McAdams presented him with an award. Evidently they looked cozy afterwards, sparking speculation in the Daily Mail that they may have been dating. Though they never went officially-official, Gyllenhaal told Marie Claire that he enjoyed working with her and could "feel her heart" when they acted together. More like South-aww, no?

Finally, Gyllenhaal starred in the Broadway play "Constellations" with "The Affair" actor Ruth Wilson. She denied dating rumors, telling Net-a-Porter (via ABC News), "He's adorable, a really good guy. We've become like brother and sister a little bit." However, a few months later, they were spotted smooching goodbye after a workout... which is not typically a brother/sister activity.

He dated model Alyssa Miller

One of Jake Gyllenhaal's only confirmed relationships during the 2010s was with a model, but not the one people initially thought. The "Ambulance" actor was first spotted out with Sports Illustrated swimsuit model Emily DiDonato, but Page Six reported that relationship had fizzled quickly and he was actually, on a more committed basis, dating her fellow S.I. vet Alyssa Miller. Sources then confirmed the relationship to Us Weekly, dishing to the publication, "They met at their gym. It's very new. They really like each other, but it's new."

A few months later, Miller herself told the magazine, "Things are good." She described "cooking dinner parties," where she and Gyllenhaal would have people over and make food for them. Gyllenhaal, she said, was the chef in the relationship, "the teacher" who guided her through preparing the dishes they presented to their guests.

They broke up when he left New York to go film "Nightcrawler" in Los Angeles, with tipsters sharing with Us that the relationship had cooled off for a while.

Rumors of an arrangement with Minka Kelly

When Jake Gyllenhaal first pursued "The Roommate" star Minka Kelly, according to Us Weekly, she just wasn't that into him, if you can believe it... and she wouldn't have even heard "All Too Well (10 Minute Version)(Taylor's Version)" yet. However, sources told the magazine that Kelly eventually gave him a shot, and apparently the two got together briefly in 2012. "It was never serious, and it's over now," an unnamed person said. No red carpets, no public brunch dates, no long walks in the park on Thanksgiving... just vibes.

While Taylor Swift famously insisted she would never get back with Gyllenhaal, "like, ever," Kelly apparently didn't feel the same way. They were rumored to have reconnected in 2014 after he split from Alyssa Miller, with a source telling Us (via E! News) that the actors had the sort of arrangement one might imagine lots of young, attractive stars have in Hollywood. "They hook up whenever they're single," the source claimed.

Jake Gyllenhaal calls model Jeanne Cadieu 'family'

Taylor Swift famously sang in the extended version of "All Too Well," "I grow older but your girlfriends stay my age." She may as well have been talking about Jeanne Cadieu, who is significantly younger than Jake Gyllenhaal; according to Us Weekly, there's a 16-year age gap between the two. The actor and the French model were first pictured together in Paris in 2018, according to E! News, who quoted a source who witnessed the romantic walk. "They were smiling the whole time and looked very happy," the unnamed spy said.

Cadieu attended the "Spider-Man: Far from Home" premiere in 2019, though she and her beau didn't walk the red carpet together. According to Esquire, Jake and his latest girlfriend spent the first part of the pandemic hunkered down together in Jamie Lee Curtis' guesthouse; the "Halloween Kills" star is Jake's godmother. "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," he gushed to the magazine.

They finally walked a red carpet arm-in-arm at the 2021 premiere of "The Lost Daughter," directed by Jake's sister Maggie Gyllenhaal, according to People. That same year, he even told Howard Stern that he's finally ready to settle down, confessing, "I love her so much, and she's just such a good person."