Taylor Swift and John Mayer's Relationship: A Look Back

Though Taylor Swift and John Mayer were only briefly linked in 2009, their rumored romance has kept fans invested for more than a decade

Taylor Swift and John Mayer are never ever getting back together, judging by the looks of things.

Swift and Mayer first connected in 2009, when they collaborated on his single "Half of My Heart." The musicians went on to perform together a handful of times, sparking romance rumors as Swift moved on from her relationship with her Valentine's Day costar Taylor Lautner.

While neither publicly confirmed the romance, both Swift and Mayer released breakup tracks — Swift's "Dear John" and Mayer's "Paper Doll" — widely believed to be inspired by the relationship, which ended in 2010.

Though it's been more than a decade since the singers went their separate ways, fans once again started speculating about their brief connection after the release of Swift's 2022 album Midnights. On the track "Would've, Could've, Should've," she sings about a past relationship from when she was 19 (Swift and Mayer were first linked when she was 19 and he was 32).

Meanwhile, Mayer also seemingly referenced their past during an April 2023 concert. While playing "Paper Doll," the guitarist wondered aloud if some fans don't like the song "because it sounds a little pissed off."

He added, "I don't really like pissed off as a song — I think it was more hurt. But I think there's something about it that's a little bitchy."

Most recently, Swift announced she's releasing the re-record of her 2010 album Speak Now — which includes several tracks that fans have long thought were inspired by Mayer.

From the Twitter exchange that sparked their collaboration to Mayer later telling Rolling Stone that he was "really humiliated" by the lyrics of "Dear John," here's a look back at Taylor Swift and John Mayer's relationship.

March 2009: John Mayer tweets that he wants to collaborate with Taylor Swift

The "Why Georgia" singer first declared his desire to work with Swift on social media. He tweeted that he had an idea for a song "called 'Half of My Heart,' " adding, "I want to sing it with Taylor Swift."

He continued, "She would make a killer [Stevie] 'Nicks' in contrast to my [Tom] 'Petty' of a song."

May 22, 2009: John Mayer and Taylor Swift perform together for the first time

Mayer joined Swift onstage during a stop on her Fearless tour at the Staples Center (now called the Crypto.com Arena) in Los Angeles, marking their first performance together. The duo sang Swift's "White Horse" and Mayer's "Your Body Is a Wonderland" together, much to the crowd's delight.

June 15, 2009: Taylor Swift says she's a "big fan" of John Mayer

When asked by Elle who she most wanted to work with, Swift named Mayer. She added that she "freaked out" when she first heard that he'd tweeted about recording with her, because she had "been such a big fan of John for such a long time."

Swift added that she had been "really excited about just the idea that he would even mention me in his Twitter!"

November 6, 2009: John Mayer recounts how he and Taylor Swift first connected on Twitter

Speaking to MTV, Mayer further explained his intentions around originally reaching out to Swift via Twitter.

He joked that there's "no better way to put it out into the universe than to tweet it," adding, "but then it's not like she reads the tweet and goes, 'I'm in,' although she may have. I don't remember."

Regarding why he wanted to collaborate with Swift, Mayer recalled, "I thought, 'This Taylor Swift girl is going to be around for a long time.' "

November 17, 2009: John Mayer releases his collaboration with Taylor Swift, "Half of My Heart"

While the single was actually leaked on Nov. 6, 2009, Mayer's album Battle Studies was officially released a few weeks later. "Half of My Heart" marked the pair's first (and last) collaboration.

On the track, Mayer sings, "Half of my heart is a shotgun wedding to a bride with a paper ring, but half of the heart is the part of a man who's never truly loved anything."

November 2009: John Mayer praises Taylor Swift throughout his Battle Studies press tour

In a series of interviews, the "My Stupid Mouth" singer sang Swift's praises whenever asked about their collaboration. He spoke mainly about her talent and her humility, sprinkling in several compliments along the way.

"Taylor is the world's biggest star who doesn't know she's a star. ... Which I think is totally sweet," he told Access Hollywood. "It's almost like Taylor Swift is a character in a movie about a small-town girl who has her dreams come true and [does] what any small-town girl would do when her dreams come true, which is to freak out. And I still like it that she freaks out, but pretty soon she's gonna have to stop because it's sort of like, 'You're that good. You're that good. You might have to go to therapy and have someone else tell you.' "

While speaking to the outlet, he also remarked on the pair's budding connection, saying, "I consider her a friend. I think she's a really remarkable person and it'll be nice to have her name on my record."

December 2009: John Mayer says Taylor Swift is "one of the smartest, most talented people around"

During an appearance on The Ellen DeGeneres Show — in which he memorably wore a Christmas sweater — Mayer spoke candidly about his admiration for the then-19-year-old songwriter.

"I'm a huge fan, and I think she's got a really great voice," he told DeGeneres, adding, "She's one of the smartest, most talented people around right now. ... I think she's that genuine."

The talk show host replied, "And I hope she remains that way too," before Mayer playfully interrupted, "I'll make sure she doesn't — you send me in there!"

December 11, 2009: John Mayer and Taylor Swift perform together at the Z100 Jingle Ball

The pair hit the stage during Mayer's set at the Z100 Jingle Ball in New York City's Madison Square Garden to perform "Half of My Heart" for the first time, quickly prompting speculation that sparks were flying.

January 24, 2010: John Mayer and Taylor Swift are spotted out to dinner in Nashville

The following month, Mayer and Swift were spotted out to dinner in Nashville together, along with a small group of friends. Their outing came on the heels of Swift's split from Taylor Lautner, whom she was linked to from October through December of 2009.

January 27, 2010: Taylor Swift sings along as John Mayer records in Nashville

A few days after their dinner, Swift arrived with her mom at the taping of CMT's Crossroads, which featured Mayer performing with country superstar Keith Urban and Swift dancing and singing along in the audience.

June 17, 2010: John Mayer honors Taylor Swift at the Songwriters Hall of Fame Induction Ceremony

Despite rumors that the duo had split in February 2010, they seemed at ease in each other's company at the annual Songwriters Hall of Fame Ceremony, where Swift was honored by Mayer. The singer spoke effusively of the country-turned-pop star.

"You could put her in a time machine in any era and she would have a hit record," he said before presenting Swift with the ​​Hal David Starlight Award. "Don't confuse everybody loving one thing as hype. Sometimes that's everyone agreeing that it's fabulous."

As she accepted her award, Swift thanked Mayer with a kiss on the cheek, and the pair shared a warm embrace.

October 25, 2010: Taylor Swift's album Speak Now is released, featuring "Dear John"

Whether their alleged romance ended before or after the Songwriters Ceremony in June, things had seemingly gone south when Swift released "Dear John" in October 2010. The song is widely believed to be about her breakup with Mayer, partly based on the title — although a "Dear John" letter is a common idiom referring to a woman ending a relationship with her partner.

The lyrics seem to reference the couple's fallout, according to fans, who point to the line, "Don't you think nineteen is too young/ To be played by your dark twisted games / When I loved you so?" as evidence that the song is about Mayer.

October 2010: Taylor Swift opens up about the inspiration for "Dear John"

Speaking to PEOPLE about the inspiration for the song, Swift declined to share who it was about. "A lot of times when people's relationships end, they write an email to that person and say everything that they wish they would have said," she said in response, noting, "A lot of times they don't push send."

Swift added that the song was "a tough one to write" and that "putting it on the album was pushing send."

June 2012: John Mayer says "Dear John" lyrics "made [him] feel terrible"

The singer was none too pleased about Swift's breakup track, telling Rolling Stone that the song's lyrics — assuming they were about him — made him "feel terrible."

He elaborated: "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."

Mayer revealed that Swift hadn't reached out to him beforehand, telling the outlet, "I never got an email. 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?"

He seemed to take issue with Swift's writing about her past relationships, referring to it 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 bulls—."

June 2013: John Mayer releases "Paper Doll," which fans speculate is about Swift

The following year, Mayer released "Paper Doll," a breakup ballad that fans consider to be his response to "Dear John." The song includes lyrics like "22" (the name of Swift's hit single, released the previous October), a mention of a red scarf (referenced in Swift's "All Too Well") as well as "Someone's gonna paint you another sky" — which is seen as a direct response to a line from Swift's breakup anthem ("You paint me a blue sky and go back and turn it to rain").

September 30, 2012: Taylor Swift says John Mayer is "presumptuous" for assuming "Dear John" is about him

In Glamour's November 2012 cover story, Swift made a rare public comment about Mayer. When asked about his comments on "Dear John," she replied, "How presumptuous! I never disclose who my songs are about." She added that she had avoided reading his response.

"I know it wasn't good, so I don't want to know," Swift told the outlet. "I put a high priority on staying happy, and I know what I can't handle."

She continued, "It's not that I'm this egomaniac and I don't want to hear anything negative, because I do keep myself in check. But I've never developed that thick a skin. So I just kind of live a life, and I let all the gossip live somewhere else. If you go too far down the rabbit hole of what people think about you, it can change everything about who you are."

February 7, 2015: John Mayer jokes about Taylor Swift avoiding him

While guest-hosting The Late Late Show, Mayer made a quick quip about the status of his and Swift's relationship that seemed to insinuate there was still some bad blood between the songwriters.

"You can see me at the Grammy Awards doing what I do best," he joked ahead of the annual awards show. "Being avoided by Taylor Swift."

December 13, 2016: John Mayer deletes tweets after fans accuse him of "shading" Taylor Swift on her birthday

On Swift's 27th birthday, Mayer tweeted, "Tuesday, December 13 may be the lamest day of the year, conceptually." While it seems the timing was just a coincidence, fans quickly called him out on the poor timing.

He followed up with another tweet insisting there was "no shade" intended, according to Vanity Fair, writing, "NOPE. No. Nuh-uh. People I am 39. I am deleting those tweets. Come right at me for doing so. Absolutely no shade."

October 26, 2018: John Mayer says Taylor Swift's Reputation is a "fine piece of work"

Alluding to the origins of his hit "New Light," Mayer, inadvertently referenced the title of his rumored ex's latest album.

During a Q&A session at an iHeartRadio LIVE show, Mayer accidentally referenced the title of Swift's then-latest album while explaining the origins of his song "New Light."

The guitarist told the audience that he "started thinking about reputation," prompting cheers from the crowd. He laughed and added, "not the album [Swift's Reputation], but that's still fine."

"That's a fine piece of work," he continued before resuming his explanation.

March 2019: John Mayer denies "Paper Doll" is about Taylor Swift

During an episode of his Instagram Live show Current Mood with John Mayer, the artist denied that "Paper Doll" is about Taylor Swift.

When a fan asked during his episode, "what song have you written that didn't get the love it deserved?" Mayer responded with the title.

"When 'Paper Doll' came out, 100 percent of the people believed it was about somebody and the person that they thought it was about brought a certain amount of a superficial pop culture back and forth about it that I think kind of shat on the song," he said.

Mayer continued, "But the song is not about that person and I could never tell anybody that's not true because then I would be breaking my rule that songwriters don't say who the songs are about or not."

March 2021: John Mayer is roasted by Taylor Swift fans on TikTok

Mayer's TikTok debut — an attempted selfie video in which he struggles to flip the camera around — was met with backlash from Taylor Swift fans, who quickly flooded his comments with references to "Dear John."

The musician responded with a video of himself nodding and listening attentively, adding the caption: "POV: You're berating me and I'm hearing you out." (The video format is often used to encourage other users to duet the video; many did, playing Swift's breakup anthem.)

The famously Internet-savvy musician seemed to take it in stride, later posting another video in which he sang, "That was a real weird day."

November 2021: John Mayer receives death threats from Taylor Swift fans

In November 2021, Swift released the re-recording of her album Red. Though much of the tracklist is believed to be about another one of Swift's exes, Jake Gyllenhaal, the record sparked renewed interest in several of the singer's past romances, which led to some fans coming after Mayer.

In an Instagram DM exchange reposted by @deux.discussions, a user messaged Mayer saying she wished he would "choke on something."

Per The New York Post's Page Six, Mayer responded to the user, saying, "I've been getting so many messages like these the past couple days. I'm not upset. I just tend to have a curious mind and feel compelled to ask. Do you really hope that I die?"

The user then wrote back, "OMG WHAT i don't want you to DIE" and apologized for her words. Mayer accepted her apology, saying he "wanted to understand" her intentions. "So it's a fun thing people are doing without taking into account that I might see it and be affected by it?" he asked.

After the user explained that she never thought Mayer would see the message, he ended the interaction on a positive note, writing that there was "some healing here today."

October 2023: Taylor Swift releases Midnights, featuring a song fans think is about John Mayer

Swift released her tenth studio album on Oct. 21, 2023, and fans quickly began dissecting the lyrics to uncover who each track was about.

Almost immediately, Swifties concluded that one of the songs on the 3am Edition of the album, "Would've Could've Should've," was likely inspired by Swift and Mayer's relationship.

On the track, Swift sings of her regrets about a past romance, alluding to an age gap and wishing she had "only played it safe" and never "danced with the devil."

The song also features a particularly scathing bridge, during which Swift sings about the relationship's aftermath: "Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first."

June 24, 2023: Taylor Swift seems to ask fans to be kind ahead of Speak Now (Taylor's Version)

Before playing "Dear John" during the Minneapolis stop of her Eras Tour, Swift asked her fans to practice "kindness" and "gentleness" online in the wake of her Speak Now re-release. She explained that she's not re-recording her albums to be defended "on the internet against someone you think I might have written a song about," seemingly referring to Mayer.

"So what I'm trying to say is, I'm putting this album out because I want to own my music and I believe that [those] who have the desire to own their music should be able to," Swift added. "That's why I'm putting out this album."

The artist continued, “I’m 33 years old, I don’t care about anything that happened to me when I was 19 except the songs I wrote. So what I'm trying to tell you, is that I am not putting this album out so you should feel the need to defend me on the internet against someone you think I wrote a song about 14 million years ago."

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