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![Jenny Lewis]()
Gyllenhaal went out with actress and Rilo Kiley frontwoman Jenny Lewis back in 2001. The two remained good friends, and Gyllenhaal brought Lewis along as his date to the Golden Globes in 2011.![Kirsten Dunst]()
Gyllenhaal and actress Kirsten Dunst began dating in 2002, but the relationship ended in 2004. Before breaking up, the two reportedly shared a Hollywood mansion and adopted a pet German Shepard.![Natalie Portman]()
It's unclear exactly when they became an item, but Jake and Natalie Portman dated sometime between 2002 and 2006. Gyllenhall later spoke fondly of Portman when presenting her with a Desert Palm Achievement Award in 2011, but added that "it does get hard when you're out to dinner with her," seeing as she's a strict vegan.![Rachel Stevens]()
According to MTV, Gyllenhaal briefly dated British singer Rachel Stevens of S Club 7 for a short time in 2006.![Reese Witherspoon]()
Gyllenhaal began dating his "Rendition" co-star Reese Witherspoon in 2007, shortly after Witherspoon divorced ex-husband Ryan Phillippe. (Phillippe once told USA Today that seeing pictures of Gyllenhaal and Witherspoon together was "bizarre.") Their relationship ended in 2009. PHOTOS: 15 Years Of Reese Witherspoon![Taylor Swift]()
For a few months near the end of 2010, Jake and Taylor Swift became an item. It's also rumored that many of the breakup songs on her 2012 album "Red" are about Gyllenhaal. (She's never named names, but she claims the man she sang about in "We Are Never Ever Getting Back Together" reached out after listening to "Red," and said it was like "going through a photo album" of their relationship.) READ: Why Taylor Swift's Neighbors Hate Her![Emily DiDonato]()
Gyllenhaal reportedly met Sports Illustrated model Emily DiDonato at a SoulCycle class in New York City in 2012. The two dated for a brief time through early 2013.![Alyssa Miller]()
Up until the end of last year, Gyllenhaal and Sports Illustrated swimsuit model Alyssa Miller were an item. The two met sometime in mid-2013.PHOTOS: Jake Gyllenhaal’s Many Exes
In news that's sure to delight that one gal-pal of yours who owns two copies of "Donnie Darko" on DVD, 33-year-old actor Jake Gyllenhaal has parted ways with his latest girlfriend Alyssa Miller. PHOTOS: 10 Celebrity Hookups You Probably Didn't Know About Us Weekly has confirmed that Gyllenhaal and the Sports Illustrated swimsuit model have ended their relationship of nearly six months, calling it quits sometime before the holidays. "Things were really good between Jake and Alyssa right up until he had to leave for L.A. to go shoot a movie in the fall," a source told the publication. "Then the distance just really got to them." READ: Wow, George Clooney's Dating History is Impressive However, if we can surmise anything from Jake's dating history, it's that he won't be single for long. Take a peek at Gyllenhaal's former flames below, then tell your "Donnie Darko"-loving friend to get a move on.
- PHOTOS: Jake Gyllenhaal’s Many Exes
