
Hey, heartbreaker! Jake Gyllenhaal has had his fair proportion of high-profile relationships — and headline-worthy breakups — by the years.
Early in his profession, the California native struck a romance with Kirsten Dunst — and almost starred reverse her in 2004’s Spider-Man 2 amid considerations over Tobey Maguire‘s well being. The pair dated for 2 years after being launched by Jake’s sister, Maggie Gyllenhaal, and even shared a house within the Hollywood Hills. In the end, the duo couldn’t make it work and known as it quits in 2004.
Following his break up from the On Changing into a God in Central Florida actress, the Oscar nominee was linked to main film stars together with Natalie Portman and Reese Witherspoon. One among his most unforgettable relationships, nonetheless, was his transient fling with Taylor Swift.
The Nocturnal Animals actor and the “Attractive” singer started courting in late 2010 however their honeymoon part didn’t final lengthy. After they break up simply earlier than the beginning of the brand new yr, a supply instructed Us Weekly, “Jake simply instructed her it wasn’t figuring out.” On the time, Swift was “actually upset and harm” and felt “actually burned” by her ex.
Two years after they known as it quits, Swift launched a scathing breakup anthem titled “All Too Effectively,” which followers have been fast to decode as a diss towards the Tony Award nominee. Whereas the Pennsylvania native’s love life didn’t lose momentum after her 2010 break up, her diehard followers have by no means forgiven Jake. In August 2020, the actor confronted the wrath of Swifties on Instagram after sharing a throwback pic of himself sporting a pair of glasses.
“U posted this pic and thought that the swifties would do nothing???? mistake,” one fan teased within the feedback. Others referred to lyrics from “All Too Effectively,” writing, “You was once a bit child with glasses in a twin-sized mattress.”
The Miss Americana star went on to launch Purple (Taylor’s Model) in November 2021, placing her transient romance with Gyllenhaal entrance and heart once more. Swift gifted her followers with a 10-minute model of “All Too Effectively” on the 30-track file, additionally creating a brief movie for the monitor starring Sadie Sink and Dylan O’Brien.
Although he’s confronted a couple of ups and downs over time, the Spider-Man: Far From House actor discovered one thing stable with girlfriend Jeanne Cadieu. Us broke the information in December 2018 that the twosome, who boast a virtually 15-year age distinction, started courting six months earlier and have been getting “fairly critical.”
The Metropolis Slickers star has stored his romance with the France native beneath wraps, however in Might 2020, he hinted that he was able to quiet down.
“I positively do [want kids],” he instructed British Vogue on the time. “I’m not somebody who has ever existed in an area the place I’ve actually identified what’s coming subsequent. However you do should be open to it. … [I’m] seeing life as one thing that’s, you recognize, fleeting, and the world being as it’s now, I’ve turned to my household, I’ve turned to my buddies and I’ve turned to like.”
Scroll down for a more in-depth take a look at Jake’s love life:
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Jake Gyllenhaal’s Relationship Historical past: From Kirsten Dunst to Taylor Swift
Hey, heartbreaker! Jake Gyllenhaal has had his fair proportion of high-profile relationships — and headline-worthy breakups — by the years.
Early in his profession, the California native struck a romance with Kirsten Dunst — and almost starred reverse her in 2004’s Spider-Man 2 amid considerations over Tobey Maguire‘s well being. The pair dated for 2 years after being launched by Jake’s sister, Maggie Gyllenhaal, and even shared a house within the Hollywood Hills. In the end, the duo could not make it work and known as it quits in 2004.
Following his break up from the On Changing into a God in Central Florida actress, the Oscar nominee was linked to main film stars together with Natalie Portman and Reese Witherspoon. One among his most unforgettable relationships, nonetheless, was his transient fling with Taylor Swift.
The Nocturnal Animals actor and the “Attractive” singer started courting in late 2010 however their honeymoon part did not final lengthy. After they break up simply earlier than the beginning of the brand new yr, a supply instructed Us Weekly, “Jake simply instructed her it wasn’t figuring out.” On the time, Swift was “actually upset and harm” and felt “actually burned” by her ex.
Two years after they known as it quits, Swift launched a scathing breakup anthem titled “All Too Effectively,” which followers have been fast to decode as a diss towards the Tony Award nominee. Whereas the Pennsylvania native’s love life did not lose momentum after her 2010 break up, her diehard followers have by no means forgiven Jake. In August 2020, the actor confronted the wrath of Swifties on Instagram after sharing a throwback pic of himself sporting a pair of glasses.
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“U posted this pic and thought that the swifties would do nothing???? mistake,” one fan teased within the feedback. Others referred to lyrics from “All Too Effectively,” writing, “You was once a bit child with glasses in a twin-sized mattress.”
The Miss Americana star went on to launch Purple (Taylor’s Model) in November 2021, placing her transient romance with Gyllenhaal entrance and heart once more. Swift gifted her followers with a 10-minute model of “All Too Effectively” on the 30-track file, additionally creating a brief movie for the monitor starring Sadie Sink and Dylan O’Brien.
Although he is confronted a couple of ups and downs over time, the Spider-Man: Far From House actor discovered one thing stable with girlfriend Jeanne Cadieu. Us broke the information in December 2018 that the twosome, who boast a virtually 15-year age distinction, started courting six months earlier and have been getting “fairly critical.”
The Metropolis Slickers star has stored his romance with the France native beneath wraps, however in Might 2020, he hinted that he was able to quiet down.
“I positively do [want kids],” he instructed British Vogue on the time. “I am not somebody who has ever existed in an area the place I’ve actually identified what’s coming subsequent. However you do should be open to it. … [I’m] seeing life as one thing that’s, you recognize, fleeting, and the world being as it’s now, I’ve turned to my household, I’ve turned to my buddies and I’ve turned to like.”
Scroll down for a more in-depth take a look at Jake’s love life:

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Jenny Lewis
The Donnie Darko actor dated the Rilo Kiley singer in 2001. Regardless of their breakup, the 2 stay shut buddies.

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Kirsten Dunst
Launched by Jake’s sister, the 2 started courting in 2002. Throughout their two-year romance, the couple shared a house within the Hollywood Hills and acquired a German Shepard. They break up in December 2004.

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Natalie Portman
The Brothers costars have been first linked in 2002 and have been noticed on a date in 2006. Regardless of their on-off romantic historical past, the 2 have maintained their friendship.

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Reese Witherspoon
Witherspoon — who first started romancing Jake whereas taking pictures Rendition — “broke his coronary heart” when she ended their three-year courtship in December 2009. “Nobody cheated,” a supply instructed Us. “There was no drama.”

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Taylor Swift
The Brokeback Mountain star started courting the “Imply” singer in late 2010, although their romance fizzled out simply earlier than New 12 months’s. “Jake simply instructed her it wasn’t figuring out,” a supply instructed Us. “Taylor is actually upset and harm…she feels actually burned by him.”
Swift has written about their whirlwind relationship on hit songs like “All Too Effectively” and “We Are By no means Ever Getting Again Collectively.”
Within the 2021 model of “All Too Effectively,” the Pennsylvania native added extra particulars about their breakup, singing, “They are saying all’s nicely that ends nicely / However I am in a brand new hell each time you double-cross my thoughts / You stated if we had been nearer in age perhaps it could have been superb / And that made me wish to die.”

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Jessica Lowndes
Months after his break up with the Grammy winner, Jake rebounded with the 90210 actress over breakfast at NYC’s Greenwich Lodge in April 2011.

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Thriller Gal
Who’s that lady? Jake stunned many when he surfaced in NYC with a thriller lady on his arm in November 2012. The actor and his new main woman have been noticed holding holds throughout a day stroll. The couple seemed fairly smitten with one another and have been bundled as much as brace the chilly climate collectively.

Credit score: Neilson Barnard/Getty Photographs; Jason LaVeris/FilmMagic
Minka Kelly
It was over earlier than it began. The Nightcrawler actor had a short fling with the Friday Evening Lights alum in June 2012. “Minka wasn’t into Jake when he first pursued her,” a mutual pal of the 2 actors solely instructed Us. However after romancing Wilmer Valderrama, Kelly “determined to provide Jake one other likelihood.” The spark rapidly fizzled, nonetheless. “It was by no means critical,” the insider added.

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Alyssa Miller
Going to the gymnasium has its advantages! Jake started courting Sports activities Illustrated Swimsuit mannequin Alyssa Miller after first assembly at their New York Metropolis gymnasium in June 2013. “Issues are good,” Miller instructed Us concerning the couple’s relationship on the Angel Ball at Cipriani Wall Avenue in NYC in October. “I’ve folks over on a regular basis and we prepare dinner,” she gushed. “He is the instructor.”

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Jeanne Cadieu
Us confirmed in December 2018 that the Southpaw actor sparked a romance with the French mannequin six months earlier. “Jeanne could be very mature for her age. She’s quirky, good and loves historical past, studying; she’s a very nice and well-rounded individual,” a supply solely revealed on the time. “She and Jake actually took issues sluggish, however at the moment are fairly critical.” The couple have stored their relationship comparatively personal however have been noticed collectively in Los Angeles in June 2020, proving their flame hadn’t fizzled out.
The Ambulance actor made a uncommon remark about Cadieu throughout an October 2021 interview with Howard Stern, including that her desire for staying out of the highlight was “a part of the rationale why I simply adore her.” He gushed: “I really like her a lot. She’s such a superb individual.”