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7 Guys Who Totally Blew It With Taylor Swift
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John Mayer

Year: 2009

What Happened: Taylor and John shared the stage, smiles, and even romance for a brief stint. Eventually, she penned a song about the breakup, aptly titled "Dear John." He responded with "Paper Doll." The aftershocks can still be felt in Taylor's feud with Katy Perry and when he attempted to make light of their relationship by mentioning Taylor on The Late Late Show in February 2015.

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