Taylor Swift was only 19 years old when John Mayer, then 32, hit her up on Twitter, saying that he wanted to sing a song with her that he had been working on. The pop-country singer, who was becoming more and more famous after the release of her "Fearless" album, told Elle in 2009, "I freaked out when I heard, because I've been such a big fan of John for such a long time." And soon enough, the pair shared the stage — and more. 

However, as soon as it began, their relationship ended. When he and Swift broke up, the "Love Story" singer apparently didn't think twice about writing some songs about him. Swift's song "Dear John" is highly speculated to be about John Mayer. Swift's lyrics in the song, "Don't you think I was too young to be messed with? / The girl in the dress cried the whole way home / I should've known" (via Genius Lyrics) seems to be directly aiming at the fact that Swift and Mayer were 13 years apart in age.

Mayer thought it was a rather petty move on her end. "It made me feel terrible," Mayer told Rolling Stone in 2012. "Because I 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. ... I think it's abusing your talent to rub your hands together and go, 'Wait till he gets a load of this!'"

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