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Taylor Swift Dated: Jake Gyllenhaal

Jake Gyllenhaal Taylor Swift
Stephen Lovekin / Jason Kempin, Getty Images

This was another one of Taylor’s many relationships that made us scratch our heads. Come to think of it, most of her relationships are questionable.

Much to our dismay (at the time), Taylor and Jake Gyllenhaal began their little hook up around October 2010, when they were first spotted in public together getting having brunch. They spent Thanksgiving together getting coffee, and two days later, were seen in Nashville at a cafe where they apparently weren’t shying away from public affection.

But, she’s Taylor Swift, so that means this relationship didn’t last long — even after he supposedly spent an exorbitant amount on a guitar for her. They broke up shortly after and you know the drill: she cried, she hurt, she wrote a song.

Taylor Swift Should've Dated...

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