7 Men in 6 Years! Is Taylor Swift a Serial Dater?

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4) Jake Gyllenhaal

With a countrified approach to dating at an apple-picking date in New York a few weeks into the relationship, this was the latest in a series of fall romances for Taylor that didn’t survive. The Nashville princess and the well-connected Hollywood darling broke it off in January 2011, 4 months into the relationship. After the New Year, they were spotted chatting on a few occasions, somewhat seriously, but the couple couldn’t patch things up.