Jake Gyllenhaal Dating
October 2001
Jake Gyllenhaal dated Rilo Kiley singer Jenny Lewis. Lewis attended the premiere of "Donnie Darko" with Gyllenhaal and he is still a fan of her music.
Jake Gyllenhaal dated Kirsten Dunst. They met via Gyllenhaal's sister, Maggie, who costarred with Dunst in the movie "Mona Lisa Smile." They finally move into together, sharing a home (and a German Shepard) in the Hollywood Hills.
Jake Gyllenhaal dated Natalie Portman. They remain good friends.
Jake Gyllenhaal dated Reese Witherspoon. The two began dating after starring together in 2007's "Rendition," though they initially denied any affair. After Witherspoon's divorce was finalized they went more public with their relationship and they were constantly pictured by the paparazzi. They split at the end of 2009.
Jake Gyllenhaal was rumored to be dating Isabel Lucas. They were spotted hanging out in Montreal together.
Jake Gyllenhaal was rumored to be dating Rachel Bilson. The two were seen out together in the fall of 2010.
Jake Gyllenhaal dated Taylor Swift. They were spotted together several times in November 2010. According to reports, they also spent the Thanksgiving holiday weekend together. By January things had cooled off and word spread that Jake broke up with Taylor over the phone.
Jake Gyllenhaal dated Olivia Wilde. They were spotted getting very cozy at the Chateau Marmont in Los Angeles. However, nothing
came out of the buzz.
Jake Gyllenhaal dated model Emily DiDonato.
Jake Gyllenhaal is currently dating Sports Illustrated Swimsuit model Alyssa Miller. Their romance went public after they were seen making out at a coffee shop in Manhattan. A source confirmed the news to Us Weekly.
What do you think of Jake Gyllenhaal's dating history?
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