The History Behind Taylor Swift’s “Dear John” Lyrics, Explained

Taylor Swift has penned beautiful songs about every stage of a relationship — and, well, of life itself. But when you need to cry it out (or drive it out) to something particularly devastating, fans typically recommend a few select songs. There’s “All Too Well,” for example, which juxtaposes cozy, romantic memories with the raw reality of a breakup that still stings. The rumored Jake Gyllenhaal ballad became even more sacred among Swifties after receiving the 10-minute treatment on Red (Taylor’s Version).

Of course, if you’ve been following Swift for a while, you know there’s another tune that predates “All Too Well” and matches its lyrical blows: “Dear John.” And there’s plenty of lore surrounding this one, too. So, who is “Dear John” about? If you need a refresher in time for Speak Now (Taylor’s Version), here you go!

Swift is famously proud of having “never named names” in her songs — and to her credit, “Dear John” is actually the general nickname for a kind of letter you send someone when you’re breaking up with them (rooted in wartime tradition). But it’s handy that John is also the name of the man most people think the song is about: John Mayer. Swift has never confirmed this, nor has she ever actually confirmed dating the “Gravity” singer, but they collaborated when Swift was 19 years old (and Mayer 32) and were later, briefly, linked together.

Nineteen, of course, is the age Swift reflects on in the song — which dropped when she was 20, so the events she sings about wouldn’t have been too far in the rearview mirror. “Dear John, I see it all now, it was wrong / Don’t you think 19’s too young / To be played by your dark, twisted games / When I loved you so?”

Swift goes on to sing that the recipient of her musical missive is an “expert at sorry and keeping lines blurry.” Throughout the song, she scolds herself for getting into the relationship at all by saying, “I should’ve known.” But after the bridge, she flips the script, telling the recipient that “You should’ve known.”

Here’s where the lore of “Dear John” gets even thicker. Twelve years later, in “Would’ve, Could’ve, Should’ve” off Midnights, Swift sings another emotional song about a relationship she had at 19 that she equates to having “danced with the devil.” While there are multiple things Swift “would’ve” or “could’ve” done, the word “should’ve” only appears when the title of the song is sung. This led to a prevailing theory that the missing “should’ve” is, well, in “Dear John.”

Mayer himself has commented on “Dear John” — and spoiler alert, he’s not a fan. “It made me feel terrible,” he 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.” He also dismissed the song (one of Swift’s revered Track 5s) as “cheap songwriting.”

“I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bullsh*t,” Mayer said.

Swift, for her part, told Glamour the same year that it was “presumptuous” for Mayer to say the song was about him. “I never disclose who my songs are about.”

More than a decade later, Swift still hasn’t confirmed the subject of “Dear John.” But she knows her fans have their theories — and preemptively asked them to be nice when Speak Now (Taylor’s Version) comes out. “I’m not putting this album out so that you ... should feel the need to defend me on the internet against someone you think I might have written a song about 14 billion years ago when I was 19,” she said before playing “Dear John” as an Eras Tour secret song on June 24. “I do not care. We have all grown up. We’re good.”