What Really Went Wrong With Jake Gyllenhaal And Taylor Swift?

Gyllenhaal and Swift broke up before the holidays in 2010 after just two to three months together, but People reports that they briefly reunited in January 2011, then had an intense run-in at the Oscars in late February 2011.

Gyllenhaal and Swift broke up before the holidays in 2010 after just two to three months together, but People reports that they briefly reunited in January 2011, then had an intense run-in at the Oscars in late February 2011.

A source told Us Weekly (via Celebitchy) in late January 2012 that all the couple's on-again-off-again drama really damaged Swift. "She's haunted by that relationship. He totally screwed with her mind," the source said, adding, "She doesn't know how to meet anybody new."

She later told El Hormiguero (via Hollywood Life), "I think once a relationship is done it's done, you can't do that back and forth thing — it's the most exhausting process. I think you have to have somebody that's dependable, that isn't going to change their mind every five seconds."

Swift admitted to NPR that her collaboration with Snow Patrol frontman Gary Lightbody, "The Last Time," was inspired by an intense on-again-off-again romance that occurred around the time she was with Gyllenhaal. "The idea was based on this experience I had with someone who was kind of this unreliable guy. You never know when he's going to leave, you never know when he's going to come back, but he always does come back," she said.

Believe it or not, some reports suggest that Gyllenhaal still carried a torch for Swift for years after their breakup. In summer 2015, a source told The National Enquirer, "Jake knows he screwed up the first time around. He wasn't ready for a commitment but now Jake's wooing Taylor via emails and texts... No guy has ever promised so much to Taylor, so she's very intrigued — and ready to see if Jake has what it takes for the long haul!" That November, a source told Star (via Life & Style) that Gyllenhaal enlisted mutual pal Cara Delevingne to reignite their old flame. Of course, Swift was dating Calvin Harris during that period, so not much came to fruition for him.

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