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Alas, he continued to unknowingly dig the grave for the first chapter of his celebrity life when he tweeted he was working on a song and he wanted to sing it with the 19-year-old Fearless artist. "Waking up to this song idea that won't leave my head. 3 days straight now. That means it's good enough to finish," the once-prolific Twitter user wrote in March 2009. "It's called 'Half of My Heart' and I want to sing it with Taylor Swift. She would make a killer Stevie Nicks in contrast to my Tom Petty of a song."

So, no expectations there at all. But they did meet up to record "Half of My Heart" for his 2009 album Battle Studies, which came out that November, and performed live together several times.

But while he did not make the same mistake he did with Aniston, it was Swift who made sure that people kinda-sorta knew what was what. That he was a man who ended a relationship.

Mayer told Rolling Stone in 2012 that he was pretty devastated by the 2010 song "Dear John," which called out a certain fellow's "dark twisted games." He insisted that, in this case, he "didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do."(Swift has never explicitly said that the tune is about Mayer, but before the song came out she said in an interview that "little hints" would assure that it would be clear who the guy was, no further explanation necessary.) 

Moreover, he continued, "I never got an e-mail. I never got a phone call. I was really caught off-guard, and it really humiliated me at a time when I'd already been dressed down. I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower?"

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