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Take a peek at Gyllenhaal's former flames below, then tell your "Donnie Darko"-loving friend to get a move on.It's unclear exactly when they became an item, but Jake and Natalie Portman dated sometime between 20.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: 15 Years Of Reese Witherspoon 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.In the past, Natalie has been linked to Jude Law, Jake Gyllenhaal, Nathan Bogle, Lukas Haas, Hayden Christensen, and long term boyfriend Gael Garcia Bernal.Of course, she does downgrade on occasion — past paramours NOT pictured include Moby (ick) and Devendra Banhart (double ick).Gyllenhall later spoke fondly of Portman when presenting her with a Desert Palm Achievement Award in 2011, but added that "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.