Friday, January 22

Looking Back at Jake Gyllenhaal's Dating History

Hey, heartbreaker! Jake Gyllenhaal has had his fair share of high-profile relationships — and headline-worthy breakups — through the years.

Early in his career, the California native struck a romance with Kirsten Dunst — and nearly starred opposite her in 2004’s Spider-Man 2 amid concerns over Tobey Maguire‘s health. The pair dated for two years after being introduced by Jake’s sister, Maggie Gyllenhaal, and even shared a home in the Hollywood Hills. Ultimately, the duo couldn’t make it work and called it quits in 2004.

Following his split from the On Becoming a God in Central Florida actress, the Oscar nominee was linked to major movie stars including Natalie Portman and Reese Witherspoon. One of his most unforgettable relationships, however, was his brief fling with Taylor Swift.

The Nocturnal Animals actor and the “Gorgeous” singer began dating in late 2010 but their honeymoon phase didn’t last long. When they split just before the start of the new year, a source told Us Weekly, “Jake just told her it wasn’t working out.” At the time, Swift was “really upset and hurt” and felt “really burned” by her ex.

Two years after they called it quits, Swift released a scathing breakup anthem titled “All Too Well,” which fans were quick to decode as a diss toward the Tony Award nominee. While the Pennsylvania native’s love life didn’t lose momentum after her 2010 split, her diehard fans have never forgiven Jake. In August 2020, the actor faced the wrath of Swifties on Instagram after sharing a throwback pic of himself wearing a pair of glasses.

“U posted this pic and thought that the swifties would do nothing???? mistake,” one fan teased in the comments. Others referred to lyrics from “All Too Well,” writing, “You used to be a little kid with glasses in a twin-sized bed.”

Though he’s faced a few ups and downs over the years, the Spider-Man: Far From Home actor found something solid with girlfriend Jeanne Cadieu. Us broke the news in December 2018 that the twosome, who boast a nearly 15-year age difference, began dating six months earlier and were getting “pretty serious.”

The City Slickers star has kept his romance with the France native under wraps, but in May 2020, he hinted that he was ready to settle down.

“I definitely do [want kids],” he told British Vogue at the time. “I’m not someone who has ever existed in a space where I’ve really known what’s coming next. But you do have to be open to it. … [I’m] seeing life as something that is, you know, fleeting, and the world being as it is now, I’ve turned to my family, I’ve turned to my friends and I’ve turned to love.”

Scroll down for a closer look at Jake’s love life.

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Jenny Lewis

The Donnie Darko actor dated the Rilo Kiley singer in 2001. Despite their breakup, the two remain close friends.


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Kirsten Dunst

Introduced through Jake’s sister, the two began dating in 2002. During their two-year romance, the couple shared a home in the Hollywood Hills and bought a German Shepard. They split in December 2004.


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Natalie Portman

The Brothers costars were first linked in 2002 and were spotted on a date in 2006. Despite their on-off romantic history, the two have maintained their friendship.


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Reese Witherspoon

Witherspoon — who first began romancing Jake while shooting Rendition — “broke his heart” when she ended their three-year courtship in December 2009. “No one cheated,” a source told Us. “There was no drama.”

Frazer Harrison/Getty

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Taylor Swift

The Brokeback Mountain star began dating the “Mean” singer in late 2010, though their romance fizzled out just before New Year’s. “Jake just told her it wasn’t working out,” a source told Us. “Taylor is really upset and hurt…she feels really burned by him.”


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Jessica Lowndes

Months after his split with the Grammy winner, Jake rebounded with the 90210 actress over breakfast at NYC’s Greenwich Hotel in April 2011.

Ernesto Ruscio/; Jordan Strauss/

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Mystery Gal

Who’s that girl? Jake surprised many when he surfaced in NYC with a mystery woman on his arm in November 2012. The actor and his new leading lady were spotted holding holds during an afternoon stroll. The couple looked quite smitten with each other and were bundled up to brace the cold weather together.

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Minka Kelly

It was over before it started. The Nightcrawler actor had a brief fling with the Friday Night Lights alum in June 2012. “Minka wasn’t into Jake when he first pursued her,” a mutual pal of the two actors exclusively told Us. But after romancing Wilmer Valderrama, Kelly “decided to give Jake another chance.” The spark quickly fizzled, however. “It was never serious,” the insider added.

Neilson Barnard/Getty Images; Jason LaVeris/FilmMagic

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Alyssa Miller

Going to the gym has its benefits! Jake began dating Sports Illustrated Swimsuit model Alyssa Miller after first meeting at their New York City gym in June 2013. “Things are good,” Miller told Us about the couple’s relationship at the Angel Ball at Cipriani Wall Street in NYC in October. “I have people over all the time and we cook,” she gushed. “He’s the teacher.”


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Jeanne Cadieu

Us confirmed in December 2018 that the Southpaw actor sparked a romance with the French model six months earlier. “Jeanne is very mature for her age. She’s quirky, smart and loves history, reading; she’s a really great and well-rounded person,” a source exclusively revealed at the time. “She and Jake really took things slow, but are now pretty serious.” The couple have kept their relationship relatively private but were spotted together in Los Angeles in June 2020, proving their flame hadn’t fizzled out.

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