Jake Gyllenhaal's Girlfriend Alyssa Miller Should've Consulted His 7 Famous Exes

Jake Gyllenhaal has quite the extensive romantic history. It seems that he's dated nearly every Hollywood It-Girl within the last decade. Recently, Gyllenhaal has been canoodling with model Alyssa Miller. According to reports, the two met at the gym ... because that's where you meet Sports Illustrated models. While we're not sure if this romance will last, we have to say that the two do look pretty cute together. But are they the most cute together? We go back through Jake's romantic life and pick out some of his most famous flings.

Jake Gyllenhaal is dating 'Sports Illustrated' Model Alyssa Miller

Jake Gyllenhaal has quite the extensive romantic history. It seems that he's dated nearly every Hollywood It-Girl within the last decade. Recently, Gyllenhaal has been canoodling with model Alyssa Miller. According to reports, the two met at the gym ... because that's where you meet Sports Illustrated models. While we're not sure if this romance will last, we have to say that the two do look pretty cute together. But are they the most cute together? We go back through Jake's romantic life and pick out some of his most famous flings.

Jenny Lewis

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The Rilo Kiley singer attended the premiere of Jake's cult classic Donnie Darko in 2001. Though the pair didn't work out as a couple, Jake is still a Rilo Kiley fan. (Wonder if he feels the same way about T.Swift?)

Kirsten Dunst

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Gyllenhaal met Dunst in 2004, when his sister, Maggie Gyllenhaal, was starring with her in the film Mona Lisa Smile. The two got so serious that they eventually moved in together. The two even shared a German Shepard during their time together. We wonder who he went to live with post-split.

Natalie Portman

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The Brothers co-stars dated briefly in 2006, but they seemed to remain friends after the split. According to reports, Jake even cracked a few jokes at Portman's expense while he presented the Oscar-winner with the Desert Palm Achievement Award for her role in Black Swan. He said: "[Natalie Portman] is the Audrey Hepburn of our generation. She's graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind and Jewish!"

Reese Witherspoon

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Reese Witherspoon is America's sweetheart (ignoring the whole "getting arrested" thing), so it seemed like a good fit that Reese would date such a nice guy like Jake. The two Rendition co-stars dated for nearly two years, from 2007 to 2009, and many thought they'd eventually get married. But it wasn't in the stars for the couple, and Reese Witherspoon went on to marry Jim Toth.

Taylor Swift

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The pop star dated Jake Gyllenhaal from October 2010 to January 2011. They were seen being super snuggly together all over the tabloids and reportedly went on coffee dates in Park Slope, Brooklyn and hung out with puppies, because that's the kind of relationship one gets into with Taylor Swift. One relationship souvenir that Jake got from the short-lived romance? His very own Swift break-up song.

Jessica Lowndes

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This 90210 star and singer was spotted having breakfast with Gyllenhaal in April 2011. A rebound post Jake's relationship with Taylor Swift? Maybe.

Emily DeDonato

Blue-eyed Emily DeDonato is a beautiful Sports Illustrated model who was rumored to be dating Gyllenhaal in March 2013. The relationship didn't work out, so Jake moved on to seeing his current fling Alyssa, yet another Sports Illustrated model. Sigh.