Even though Taylor Swift and John Mayer were only linked for a brief period of time over a decade ago, their controversial romance is still making headlines and inspiring debate today. With Swift re-releasing her earlier albums, subjects of old songs are revisited as new fans discover the details of the singer’s past relationships — and they’re not all enchanted.
The months-long relationship between the two musicians that lasted between 2009 and 2010 has turned into inspirational fodder for some of the greatest songs in Swift’s discography. While she never confirms nor denies what or who a given song is about, fans have latched on to a handful of them as the only proper window into what exactly went down between the two.
When did Taylor Swift and John Mayer date?
It all started in early 2009, when Mayer, then 32, tweeted about a song idea that wouldn’t leave his head. The song was called “Half of My Heart,” and he pictured Swift, then 19, as a featured vocalist. He compared her to Stevie Nicks at the time. Swift was a fan of his and didn’t hide her excitement after being noticed by a musician she admired so much.
The song was eventually recorded and included on his fourth studio album, Battle Studies, released in November 2009. In the meantime, earlier that year, Mayer was also a guest at her Fearless Tour at Staples Center, singing “Your Body is a Wonderland” and “White Horse” with her.
Fast-forward a few months, to the infamous 2009 Video Music Awards when the Love Story singer’s acceptance speech was interrupted by Kanye West. John Mayer did say a few words about what happened at the event, but let’s focus on someone else for a moment: Taylor Lautner, then 17, who was on stage when it all went down.
Taylor and Taylor allegedly met around prep for the 2010 movie Valentine’s Day, in which they played a teenage couple that acts as comic relief. Rumor has it that they started dating around then and were together at the time of the VMAs, in September. That is until they weren’t.
Backstage at the 2009 Jingle Ball, in December 2009, rumors started about Taylor and John being closer than usual. That standard continued until early 2010 when they were no longer seen together. At the 2010 Country Music Television Awards, there is a photo of the two talking in the audience, her standing and him still in his seat. They already seemed distant by then.
What songs did Taylor Swift and John Mayer write about each other?
Swift’s third studio album Speak Now came in October 2010. Written entirely by the singer-songwriter in response to critics’ doubts about her writing skills, the tracklist revealed Swift at her most personal.
Remastered in 2023 and re-released with the title Speak Now (Taylor’s Version), the album created quite a stir. The content of the lyrics and the mobilization by Swifties against Jake Gyllenhaal at the time of Red (Taylor’s Version)’s release a couple of years prior led to the singer directly asking fans to not attack the people they thought the songs were about online.
“Back to December,” the second single off Speak Now, is an apparent apology to Taylor Lautner, and it is so full of detail you can practically see the moments she’s referring to. Some key takeaways from the lyrics are: the breakup was acknowledged by both to have been her fault, they were together during the summer and fall, and something happened in December. December 2009, right around the time she was too close to a certain John Mayer.
“Ours”
Other songs rumored to be about Mayer, and that seem to paint him in a more positive light, are “Superman” and “Ours,” both from the deluxe version of Speak Now. Their lyrics are filled with admiration and even have a certain us-vs-them feel as if it was the two of them against the world and she needed to protect that special bond.
If we assume these songs are about Mayer, it gives us a hint that their relationship may not have been approved by those close to them, or at least by her.
“Dear John”
However, the real star is Speak Now’s fifth track, “Dear John,” which gave us the clearest image of Swift and Mayer’s relationship up to that point. The song is a heartfelt electric guitar ballad that runs for almost seven minutes, sounding suspiciously like a John Mayer track, but sung and written in a way only Taylor Swift could have done.
With lines like “My mother accused me of losing my mind, but I swore I was fine,” (a callback to “Ours”), and “You’ll add my name to your long list of traitors who don’t understand,” Taylor implies that getting involved with him was not worth it.
The age gap between her and an ex-lover is also discussed in the 10-minute version of “All Too Well” from Red (Taylor’s Version), which is rumored to be about Gyllenhaal. In this song she asks, loud and clear: “Don’t you think nineteen’s too young to be messed with?.”
It seems she figured out there was something wrong and ran, or at least that’s what we understand from lines like “I took your matches before fire could catch me” and “I stopped picking up and this song is to let you know why.” But not fast enough to avoid trauma.
Any track five from a Taylor Swift album is usually the one that hurts the most, and “Dear John” is one of the finest examples of that.
“The Story Of Us”
There is one other song off of Speak Now assumed to be about Swift’s involvement with Mayer, or more specifically that awkward encounter at the 2010 CMT Awards. In “The Story of Us,” she writes about the feeling of meeting someone you once had feelings for, and how loud the silence is when you’re not speaking to each other anymore.
“Paper Doll”
Mayer did not like the way he was portrayed in those songs at all, calling them “cheap” songwriting to Rolling Stone and saying he felt “humiliated.” Rumor has it that he wrote “Paper Doll,” the first single from his 2013 album Paradise Valley, about Swift.
Some of the lyrics seem to be pointing straight at the blonde singer, one of which is “You’re like twenty-two girls in one. And none of them know what they’re runnin’ from.” It is speculated that the use of the number “22” is in reference to Swift’s single, and the part about running goes back to a lyric in “Dear John” that says “I’ll look back and regret it. How I ignored when they said run as fast as you can.”
Another interesting detail is in the lyrics for “Innocent,” a song widely known to be about Kanye West and even performed at the 2010 VMAs in response to the 2009 incident. The line “32 and still growing up now” applies, whether intentionally or not, to both men at the time they hurt her. Both West and Mayer were born in 1977 and were 32 when their respective incidents took place. Swift was 19.
This brings us to a much more recent song — “Would’ve, Could’ve, Should’ve” from Swift’s 10th studio album Midnights.
“Would’ve, Could’ve, Should’ve”
Several passages of the song are familiar to anyone who’s heard “Dear John.” She recalls the regret, and the trauma, not to mention how young she was when it all went down, specifically in moments like “Give me back my girlhood, it was mine first,” and the chorus: “I damn sure never would’ve danced with the devil at nineteen.”
Given the fact that Midnights is an album written about the thoughts and fears that kept her up late at night, you can imagine why fans got angry. It seems like the damage done by this situation is probably much deeper, and has lingered much longer than most people ever imagined. She was, indeed, too young to be messed with, and he, indeed, should’ve known.