Jake Gyllenhaal » Dating History


Historical look at Jake Gyllenhaal relationships, listed in date order.

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Jenny Lewis
Jake Gyllenhaal and Jenny Lewis October 2001
Jake Gyllenhaal and Rilo Kiley singer Jenny Lewis dated in 2001. She attended the premier of 'Donnie Darko' with him, and he is still a fan of her music. [more]
Kirsten Dunst
Jake Gyllenhaal and Kirsten Dunst September 2002 - December 2004
These two met via Gyllenhaal's sister, Maggie, who costarred with Dunst in the movie "Mona Lisa Smile." They eventually move into together, sharing a home (and a German Shepard) in the Hollywood Hills. [more]
Natalie Portman
Jake Gyllenhaal and Natalie Portman 2006 RUMOR
Jake Gyllenhaal and Natalie Portman dated briefly in 2006. [more]
Reese Witherspoon
Reese Witherspoon and Jake Gyllenhaal March 2007 - December 2009
Reese and Jake started dating after starring together in 2007's "Rendition," though they initially denied any relationship. After Witherspoon's divorce was finalized they went more public with their romance, and they were constantly photographed by the paparazzi. They split at the end ... [more]
Taylor Swift
Taylor Swift and Jake Gyllenhaal October 2010
Taylor Swift and Jake Gyllenhaal sent the rumor mill into overdrive when they were spotted together several times in November 2010. They reportedly also spent the Thanksgiving holiday weekend together. Jake Gyllenhaal dumped her via a text message. If these latest rumors are to be believed, there was ... [more]
Anna Kendrick
Anna Kendrick and Jake Gyllenhaal 2011 RUMOR
They were only seen hanging out with each other. Just a friendly outing, nothing serious. [more]
Minka Kelly
Minka Kelly and Jake Gyllenhaal May 2012 RUMOR
Jake Gyllenhaal has been on a string of dates with Minka Kelly. The 31-year-old actor - who initially pursued the 'Friday Night Lights' star late last year - persuaded the actress to go out with him after she split from Wilmer Valderrama even though she initially wasn't interested in him ... [more]
Alyssa Miller
Jake Gyllenhaal and Alyssa Miller June 2013 - May 2014
Jake Gyllenhaal Dating Sports Illustrated Swimsuit Model Alyssa Miller Jake Gyllenhaal has found a mate in a Sports Illustrated Swimsuit model. The 32-year-old actor is currently dating Alyssa Miller, a source confirms to Us Weekly. Earlier this week, the New York Post's Page Six was first to report ... [more]
Rachel McAdams
Rachel McAdams and Jake Gyllenhaal June 2014 RUMOR
Jun 10, 2014 Fact: Rachel McAdams is one of the luckiest leading ladies in Hollywood. First, she romanced her The Notebook co-star Ryan Gosling on and off for a few years, and now she's reportedly getting cozy with Jake Gyllenhaal ' SUH-WOON. A new report claims the genetically gifted duo ... [more]

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