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Jake Gyllenhaal has an illustrious past when it comes to dating, often getting romantically involved...

Who Has Jake Gyllenhaal Dated? Here’s A Look At All His Past Loves

A comprehensive list of those who know him All Too Well.

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Long before there was Red (Taylor’s Version), Jake Gyllenhaal was busy breaking Gyllen-hearts left and right. Over the years, the 41-year-old actor has had several notable romances — from fellow actors Kirsten Dunst and Reese Witherspoon to pop icon Taylor Swift — some of whom have been co-stars, musicians, or models.

Gyllenhaal’s dating history has gone under the microscope lately in the wake of Taylor Swift’s 2021 re-release of her 2012 album Red. While it’s not been outright confirmed by Swift herself, certain tracks on the album, especially breakup anthem “All Too Well,” are thought to be nods to her brief, three-month relationship with the actor. Gyllenhaal, who’s nine years older than Swift, and whose current girlfriend is 15 years his junior, has faced a lash of scrutiny from Swifties who are, shall I say, skeptical of his dating habits.

Whether you’re a Swiftie doing your due diligence on Taylor’s exes or a Brokeback Mountain stan, it’s fun to take a trip down memory lane and remember all the names in Gyllenhaal’s little black book. So sit back and allow Gyllenhaal’s dating history to take you on a journey — back to the early aughts, back to the Donnie Darko days, back to when he was little more than a scraggly mustache in an oversized blazer on the arm of then-girlfriend Jenny Lewis.

Read on for everything you need to know about Jake Gyllenhaal’s dating history.

2001: Jenny Lewis

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Gyllenhaal and Jenny Lewis, the former frontwoman for indie rock band Rilo Kiley, shared a brief romantic relationship in 2001. He and Lewis have remained friends since, staying close and supporting each other’s work. Gyllenhaal even took Lewis as his date to the Golden Globes in 2011.

2002 - 2004: Kirsten Dunst

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Gyllenhaal’s romance with actor Kirsten Dunst reportedly took off at lightning speed, moving in together and adopting a puppy well before their second anniversary. When they split, a rep put out a statement saying they remained the “best of friends.” Years later though, in 2009, Dunst told Allure that “it would be nice to see him, but we're not good friends." RIP.

2006: Natalie Portman

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Though their romance didn’t last long, Natalie Portman and Jake Gyllenhaal made for a very cute couple when they dated for a few months in 2006 — though, according to E!, the pair reportedly also dated for an even briefer period in 2002. After their split in 2006, Gyllenhaal and Portman stayed friends and even shared the screen together in 2009's Brothers. Gyllenhaal even lightly roasted Portman when he presented her with the Desert Palm Achievement Award in 2011, quipping, "She's a vegan, which makes it really frustrating when you're picking a place to eat."

2007 - 2009: Reese Witherspoon

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This one hits hard. Gyllenspoon’s love was really something special. After her divorce from Ryan Philippe, Witherspoon started dating Gyllenhaal in early 2007, and often spoke about their relationship to the press. In October 2008, she told Vogue, "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, you know, that's all you can hope for in life. I am very blessed in that way.”

He reportedly spent a lot of time with Witherspoon’s kids, Ava and Deacon, and even accompanied the family up to Ojai on weekends where they’d stay on Witherspoon’s farm, be merry, and grow vegetables.

When they split in late 2009, fans were heartbroken. But at the time, a source told E! that their spark simply “fizzled.”

Still, in 2016, Gyllenhaal spoke glowingly of his ex, telling Entertainment Weekly that Witherspoon is, “as I would say about most of the women who I'm close friends with or had relationships in my life, one of the smartest, strongest people I've ever met."

2010: Taylor Swift

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And just like that, welcome to the Taylor era. Gyllenhaal and Swift shared a very autumnal romance in 2010 when they were first spotted together in New York City. It was October, they wore scarves, and according to E!, one of their first dates was reportedly a trip to an apple farm. It doesn’t get more cozy-cute than that.

They reportedly celebrated Thanksgiving together that year with Gyllenhaal’s sister Maggie before continuing on to Nashville to close out the festivities. It was around this time that the couple was spotted walking arm-in-arm down a sidewalk in Brooklyn, both with double-wide smiles, and Swift carrying none other than a maple latte in her left hand.

Their relationship, of course, ended in December 2010. (Though if you take the lyrics of “All Too Well (10-Minute Version) (Taylor’s Version)” as a true account of their romance, they briefly reconnected in March 2011.)

2012: Anna Kendrick, Minka Kelly, Jessica Lowndes

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While rumors about romances with actors Anna Kendrick (another co-star of his from End of Watch), Minka Kelly of Friday Night Lights, and Jessica Lowndes of 90210 were prevalent during this time period, none were ever confirmed. The same year, Gyllenhaal was spotted holding hands with an unknown woman in New York City, though details of a relationship never surfaced.

2013: Alyssa Miller

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Sports Illustrated model Alyssa Miller reportedly met Gyllenhaal at the gym — this may just be the motivation I need to start working out — which sparked a relationship that lasted for about six months. The pair met in New York City but reportedly split up when Gyllenhaal moved to Los Angeles to start filming Southpaw.

2018 - Present: Jeanne Cadieu

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And finally, that brings us to French model Jeanne Cadieu, who was first photographed with Gyllenhaal while on a stroll in Paris in 2018. They’ve kept their love out of the public eye for the most part; they’re hardly ever seen together in public and they don’t follow each other on Instagram, according to E!.

In May 2020, Gyllenhaal told British Vogue that he intends to double-down on his personal relationships for the foreseeable future, ostensibly including his relationship with Cadieu. "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,” he said. “I'm a little less interested in the work, I would say, and more interested in that."

There you have it, folks. Jake Gyllenhaal’s illustrious dating history from A-Z (or Lewis to Cadieu).