Jake Gyllenhaal: The complete hookup history

Douglas Charles Managing Editor

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When you think of the legendary ladies men in Hollywood one name that should always come up is Jake Gyllenhaal. While his alleged dating history with sexy female celebrities isn’t as long as some, the names on the list are as impressive as just about anyone we’ve chronicled.

Jenny Lewis (2001)

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Jake and the lead singer of Rilo Kiley dated briefly. She attended the premiere of his second major film, Donnie Darko, with him. He was just getting started.

Kirsten Dunst (2002-2004)

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For two years, Gyllenhaal dated Dunst. They met through his sister, Maggie, who worked with her in the film Mona Lisa Smile. Dunst and Gyllenhaal even moved in together at one point. You can see his momentum building.

Natalie Portman (2006)

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Boom. He’s on a full roll now. Portman was just hitting her stride with V for Vendetta. Unfortunately this didn’t last, but the two remain good friends. How nice.

Reese Witherspoon (2007-2009)

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The second Academy Award winning actress on this list. These two started dating after working together in the film Rendition. Oh yeah, she was still married at the time so they denied it. Then she got divorced and it was all good for two years.

Rachel Bilson (2010)

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Bilson and Hayden Christensen have been together since 2007. Except for a tiny little window in 2010. Jake took advantage.

Taylor Swift (2010-2011)

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Swift and Gyllenhaal spent several months dating, much to the delight of the paparazzi who forced the couple to call the LAPD once because so many photographers were following them. Then they broke up and she most undoubtedly wrote a song about it.

Anna Kendrick (2011-2012)

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Anna and Jake met on the set of End of Watch. They denied dating initially, but pictures of the two of them cuddling off the set suggested otherwise.

Minka Kelly (2012)

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Kelly and Gyllenhaal dated after she split from Wilmer Valderrama. At first she wasn’t interested, because who can compete with Wilmer Valderrama, but Minka ended up going out with him anyway. Sadly, this too did not last.

Other less-substantiated alleged flings…

Rashida Jones, Jessica Lowndes, Isabel Lucas, Olivia Wilde

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Previous hookup histories on Guyism.