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Before he dated Swift, Mayer was walking red carpets with Jennifer Aniston from 2008 to 2009.
After some on-and-off dating for about a year, including an impromptu press conference from Mayer about their first breakup, Aniston and Mayer finally called it quits on respectable terms.“I ended a relationship to be alone because I don’t want to waste somebody’s time if something’s not right,” he told reporters outside of his NYC gym in the summer of 2008.
“This heart didn’t come with instructions,” he tweeted.
This is another relationship that came to a close, with no chance of a friendship.
Mayer makes headlines these days when it comes to his numerous girlfriends.
He has quite the reputation in Hollywood for dating some of the biggest celebrities in the world, yet usually ends up looking like the bad-guy when the relationship ends.
In fact, they ran into each other recently, while Perry was on a date with her current boyfriend, Orlando Bloom. Whether of not this relationship resulted in Swift‘s song, “Dear John,” or not, Mayer and Swift’s romance was arguably his biggest tabloid relationship to date.