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15 of Jake Gyllenhaal’s Relationships—On-Screen & Off-Screen Romances

1. Jenny Lewis

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One of Jake Gyllenhaal’s first relationships that got press attention was his romance with actress and lead vocalist of the indie rock band Rilo Kiley, Jenny Lewis. The pair dated during Jake’s Donnie Darko days in 2001. They broke up but have maintained a close friendship. Jake has brought his girlfriend-at-the-time Reese Witherspoon to see Jenny perform at Coachella in 2009, and he brought Jenny with him as his date to the 2011 Golden Globes. They didn’t reignite their relationship; he was just bringing an old friend.

2. Donnie Darko and Gretchen Ross (Donnie Darko)

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In the cult favorite Donnie Darko, Jake Jyllenhaal stars as the eponymous troubled teenager Donnie. He can see a creature in a large rabbit costume who tells Donnie that the world will be ending in 28 days. He meets and begins a relationship with the new student at his high school Gretchen Ross, played by Jena Malone. Without any spoilers, they develop a strong relationship and some interesting developments put them to the test.

3. Jimmy Livingston and Chloe (Bubble Boy)

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Gyllenhaal starred as the eponymous Jimmy Livingston; the boy who was born without an immune system and is forced to live in a bubble. His world is very sheltered, as his very conservative and very religious mother only gives him exposure to Land of the Lost and Highlights Magazine. You know, the children’s magazine in the waiting room of your dentist’s office that has those games you play. Jimmy meets his new neighbor, a girl named Chloe, played by Marley Shelton, and the two strike up a friendship. As time passes, Chloe announces she is going to marry her boyfriend at Niagara Falls. Jimmy becomes sad, but finds a gift from Chloe and realizes she cares for him. He rushes off in a newly-constructed mobile-bubble-suit to stop the wedding.

4. Kirsten Dunst

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Introduced by his older sister Maggie Gyllenhaal, Jake started dating Kirsten Dunst in 2002. Their relationship lasted two years. They shared a Hollywood Hills home together, and even a German Shephard mix named Atticus. They broke up in 2004. Jake got the dog, but Kirsten retained partial custody. Poor puppy–his world torn apart by a Hollywood breakup. In 2009, Kirsten told a magazine that although she’d like to see Jake, the two aren’t good friends and don’t keep in touch. Of course the breakup was bitter–there was a dog involved!

5. Joe Nast and Bertie Knox (Moonlight Mile)

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Jake takes on the role of Joe Nast, a guy whose fiancée was recently murdered. Jake certainly stars in a lot of films involving death. Nast goes into his business with his fiancée’s father like they had planned. Joe meets a girl named Bertie (played by Grey’s Anatomy star Ellen Pompeo) who helps him retrieve Nast’s wedding invitations. Joe runs into her again later in a bar and the two sleep together. Seems to be a common way Jake meets girls in his films.



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