“Dear John” is boldly about Swift’s relationship with Mayer. Though Swift (often with a heap of sexism) has a reputation for burning exes in her music, “Dear John” from 2010’s “Speak Now” is the only song that actually names an ex-boyfriend in the title. Swift’s anger and deep sadness is clear from the lyrics. In the chorus she sings, “Dear John, I see it all now that you’re gone / 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.” She also accuses him of treating her like a chess piece in a game in which he “changed the rules every day.”
Swift wrote on her website at the time about the song, “The song ‘Dear John’ is sort of like the last email you would ever send to someone that you used to be in a relationship with. Usually people write this venting last email to someone and they say everything that they want to say to that person, and then they usually don’t send it. I guess by putting this song on the album I am pushing send.”
Unsurprisingly, Mayer did not appreciate the track. He told Rolling Stone in 2012, “It made me feel terrible. 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.” He said Swift never reached out about the song, explaining, “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?” When Rolling Stone asked about the line “Don’t you think I was too young to be messed with?” he would not comment on it. He also called it, “Cheap songwriting.”
But in a way, Swift predicted this response. In the song she sings, “And you’ll add my name to your long list of traitors who don’t understand.” And when Swift was asked about the song — and Mayer’s reaction to it — in a 2012 interview with Glamour, she called him “presumptuous” and said she didn’t want to know the details of his comments. “I know it wasn’t good, so I don’t want to know,” she explained. “I put a high priority on staying happy, and I know what I can’t handle.”