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Taylor Swift & John Mayer: Everything You Need to Know

Are you ready for it? Here's the inside scoop on what went down.
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We’re living in 2023 (Taylor’s Version). The brilliant songwriter we know as Taylor Alison Swift is currently on her whirlwind Eras Tour, after unleashing emotional chaos with seven different album releases in three years.

Since 2020, Taylor has released folklore, evermore, Fearless (Taylor’s Version), Red (Taylor’s Version), Speak Now (Taylor’s Version)Midnights and 1989 (Taylor’s Version). Talk about a busy schedule for a woman who famously uttered the phrase “not a lot going on at the moment.”

WATCH: Taylor Swift’s iconic Joe Jonas moment on Ellen

With the release of these re-recorded albums – in particular the 10-minute version of All Too Well – Taylor fans have been busy reliving the joy of her older music. Not to mention, the good old days of listening to her break-up tracks about Mr “Steal Your Scarf” himself, Jake Gyllenhaal.

Taylor’s latest effort, 1989 (Taylor’s Version), was released on October 27, 2023. Next up? Fans think she’ll be releasing Reputation (Taylor’s Version).

Another popular drop, Speak Now (Taylor’s Version), was written by Taylor between the ages of 18 to 20, and it transported fans back to a time of soul-destroying tracks about her famous exes Joe Jonas, Taylor Lautner, and John Mayer.

It was predicted that Mayer would predominantly feel the wrath of the Swiftie fandom. In fact, Lautner recently joked that he “feels safe” but is “praying for John Mayer” ahead of the release.

If you weren’t aware of this particular moment in pop culture history, you might be wondering, did Taylor Swift and John Mayer really date? The answer is yes, of course, so let’s dive into their relationship.

Taylor Swift
As Taylor re-records her masters, fans are reliving the glory days of her best break-up songs. (Credit: Getty Images)

Taylor and John dated briefly between 2009 and 2010, when she was 19 and he was 32. A sore point that scored its own lyric in the song Dear John. 

Their age gap and ill-fated relationship received further scrutiny when Taylor released Would’veCould’veShould’ve on her Midnights album in 2022. 

The pair collaborated on music together while they were dating and, in the years to come, would tear each other to shreds with their own lyrics. 

So, let’s go back to the beginning…

Taylor Swift and John Mayer relationship timeline
Taylor Swift dated John Mayer when she was 19 and he was 32. (Credit: Getty Images)

The Tweets (2009)

John first reached out to Taylor on Twitter in March, 2009. He tweeted about wanting to record a song with the Fearless singer, comparing her to Fleetwood Mac’s iconic Stevie Nicks.

“Waking up to this song idea that won’t leave my head. 3 days straight now. That means it’s good enough to finish,” he wrote. “It’s called Half of My Heart and I want to sing it with Taylor Swift. She would make a killer Stevie Nicks in contrast to my Tom Petty of a song.”

Having just released her second album at this point in time, Taylor was understandably star-struck to hear John wanted to work with her.

“I freaked out when I heard, because I’ve been such a big fan of John for such a long time,” she told Elle in an interview. “I’m really excited about just the idea that he would even mention me in his Twitter!”

WATCH: Taylor Swift and John Mayer perform together. Story continues after video.

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Half of My Heart (May – December 2009)

As Taylor began travelling around the US with her Fearless tour, she was joined on stage by John. He popped up during her performance at the Staples Centre in Los Angeles, coming out to sing Your Body Is A Wonderland and White Horse.

His surprise guest appearances caused a Swiftie meltdown, with the pair going on to release Half of My Heart in June 2009.

The song was about someone who saw their heart as being in two: half of their heart wanted to stay with their partner, the other half wanted to run away from the relationship. Perhaps the most telling lyric of the track was…

“Half of my heart is a shotgun wedding / To a bride with a paper ring / And half of my heart is the part of a man / Who’s never truly loved anything.”

After releasing the song, they performed it together during John’s set at Z100’s Jingle Ball in December 2009. At this point they were “confirmed” to be an item by close sources.

taylor and john
John and Taylor performed together at the Z100 Jingle Ball. (Credit: Getty Images)

But wait – when did Taylor Swift and John Mayer actually date?

Now, the pair have never confirmed a timeline for dating. They were rumoured to be an “official couple” from December 2009 until some time in mid-2010. There were reports that the pair split ways around February 2010 – but that would make make some of the following events quite odd.

There appeared to be no bad blood between the two when John presented Taylor with an award at the 41st Annual Songwriters Hall of Fame Ceremony, in June 2010. 

“You could put her in a time machine in any era and she would have a hit record. Don’t confuse everybody loving one thing as hype. Sometimes that’s everyone agreeing that it’s fabulous,” John said of Taylor in his speech, leading many to believe they were still together.

Considering her well-documented feelings about their split, it seems strange to think Taylor and John had broken up at this stage. The Songwriters Awards took place shortly after the CMT Awards, which both stars attended. At the time, news outlets reported they had were there together.

However, fans believe that this was when the cracks began to appear in their relationship. 

Some believe that Taylor’s song The Story of Us is about their encounter at the CMT Awards. In the lyrics, she tells the story of an on-off romance coming to a bitter end.

“This is looking like a contest / Of who can act like they care less / But I liked it better when you were on my side,” she sang.

“Now I’m standing alone in a crowded room / And we’re not speaking and I’m dying to know / Is it killing you like it’s killing me.”

A few months following their final public appearance, Taylor would use her song-writing prowess to detail their split in excruciating detail when she released Dear John.

Taylor and John hugging in 2010
Taylor and John hugged it out on-stage in June 2010. (Credit: Getty Images)

Dear John (2010)

A “Dear John letter” is one sent to your lover, to tell them you no longer have feelings for them. Also, his name is obviously John. So, there’s that.

The absolute scorcher of a song was released in October 2010 with Taylor’s Speak Now album, and is considered one of the top tracks. Lyrics include:

“Dear John, I see it all now it was wrong / Don’t you think nineteen is too young / To be played by your dark twisted games, when I loved you so? / I should’ve known”

“Well maybe it’s me and my blind optimism to blame / Maybe it’s you and your sick need to give love then take it away / And you’ll add my name to your long list of traitors who don’t understand / And I’ll look back and regret how I ignored when they said “run as fast as you can”

“You are an expert at sorry, And keeping the lines blurry / Never impressed by me acing your tests / All the girls that you’ve run dry Have tired, lifeless eyes / ‘Cause you burned them out / But I took your matches before fire could catch me, / So don’t look now, I’m shining like fireworks over your sad, empty town”

When performing Dear John on tour, Taylor wore a purple gown reminiscent of the dress she was wearing when John presented her with the Songwriters Award. 

As Swifties know, there’s no such thing as coincidence when it comes to Taylor, Queen of dropping Easter Eggs for fans.

Taylor Swift dress john mayer
We’re not the only ones who see it, right? (Credit: Getty Images)

John Mayer speaks out about Dear John (2012)

Some fans may not remember, but two years after Dear John was released John did something very few of Taylor’s exes have done: he spoke out about the song publicly. 

In a 2012 interview with Rolling Stone, John complained about his ex-girlfriend’s song and said he “didn’t deserve” to be called out.

“It made me feel terrible. It was a really lousy thing to do,” John told Rolling Stone at the time. “I never got an email. I never got a phone call. I was really caught off guard.”

“[Dear John is] cheap song-writing,” he snipped. “It’s abusing your talent to rub your hands together and go, ‘Wait til he gets a load of this!’ That’s bulls–t.”

Cut to a year later, and John did some song-writing of his own.

Paper Doll (2013… and 2023)

In his track Paper Doll, John detailed an ex who he “was good to” and puts the blame of the split back onto the girl who was “a little paper doll.” Throughout the song, she’s described as being too fragile to hand the relationship.

There were many similarities between the lyrics of Paper Doll and Dear John, all but confirming the track was about Taylor.

“Here’s a dress of gold and blue” could be in reference to the outfits she wore when they performed on stage together, while the “someone’s gonna paint you another sky” lyric calls back to the Dear John lyric “paint me a blue sky, and go back and turn it to rain.”

Meanwhile, the tracks central chorus says: “You’re like twenty-two girls in one / And none of them know what they’re runnin’ from.”

We wonder which song of Taylor’s that refers to? Oh yes, probably 22 considering it was released the year prior.

John and Taylor
The relationship went south some time in 2010, leading to some pretty great break-up tracks. (Credit: Getty Images)

John even addressed the lyrics of Paper Doll in April 2023 – an entire decade later. 

After Taylor and Joe Alwyn reportedly split in early April, John decided to play Paper Doll that weekend. He also called the song “a little bitchy.” 

In a clip posted online, John said of the song’s bad reputation: “I wonder if people don’t like it because it sounds a little p****d off.”

“I don’t really like ‘p****d off’. As a song, I think it was more hurt but I think there might be something about it that’s a little bitchy,” he continued. “I try not to get bitchiness in the song but it happens sometimes.”

Swifties were not very happy with John for performing the supposed Taylor diss-track on the same day her split from Joe was made public.

The Birthday Tweet (2016)

In 2016, four years after John said Taylor’s song was cheap, he caused chaos on Twitter with some choice words on Taylor’s 27th birthday. But, he claims it was innocent and went on to delete it from the internet.

On her birthday, John tweeted that “Tuesday, December 13, may be the lamest day of the year, conceptually.”

When he deleted the tweet, and was called out for doing so, John tweeted again to say: “NOPE. No. Nuh-uh. People I am 39. I am deleting those tweets. Come right at me for doing so. Absolutely no shade.”

john mayer taylor swift tweet
John later deleted the awkwardly-timed tweet. (Credit: Twitter)

Reputation (2018)

When Taylor was in her reputation era she famously neglected to do interviews, saying there would “be no explanation, there is only reputation.” A fitting time for John to pipe back up.

During a Q&A at the iHeartRadio Theatre in 2018, John told the crowd he had been “thinking about reputation.”

When fans yelled out in excitement, he quickly clarified: “Not the album, but it’s fine. It’s a fine piece of work.”

Shady with Shawn Mendes (2019)

What can we say, John loves to flip like a pancake. After claiming there was “no shade” to his actions in 2016 and calling Reputation “fine” in 2018, John went back to the old standby of mocking Taylor in 2019.

During Taylor’s Lover era she let Shawn Mendes perform a duet remix of her smash hit. For some reason, Shawn decided to do an Instagram Live with John, where the latter mocked her song-writing on the title track Lover.

Joking about the Christmas lights lyric, John said: “[Taylor’s] insane. Everyone keeps their Christmas lights up until January. And I go, ‘Can you really?’ Because normally I take my Christmas lights down on December 29.”

Continuing on while Shawn laughed, John shared his own take on the lyrics: “We can keep the Christmas lights up ’til January. And then about January 5, we’ll take the lights down. And then we’ll put ’em in a box and we’ll label that box ‘Christmas lights.’ Yeah, we’ll put ’em in the attic until next December. Well, that’s a crazy love, I’ll tell you.”

Hmm.

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Shawn and John received backlash over the video. (Credit: Instagram)

Would’ve, Could’ve, Should’ve (2022)

With the release of Midnights (3am Edition), Taylor unleashed one of her most heart-breaking tracks to date with the song Would’ve, Could’ve, Should’ve.

The song details her relationship with an older man when she was 19. Interestingly, the track was released when Taylor was 32 (the same age the singer was when he dated a then teenage-Taylor). 

The lyrics paint a picture of her loss of innocence through the relationship: 

I damn sure never would’ve danced with the devil / At nineteen, and the god’s honest truth is that the pain was heaven / And now that I’m grown, I’m scared of ghosts / Memories feel like weapons / And now that I know / I wish you’d left me wondering.”

“God rest my soul/ I miss who I used to be / The tomb won’t close / Stained glass windows in my mind / I regret you all the time / I can’t let this go / I fight with you in my sleep / The wound won’t close / I keep on waiting for a sign / I regret you all the time.”

“If clarity’s in death, then why won’t this die? / Years of tearing down our banners, you and I / Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first.”

You can read more about the Easter eggs in Midnights here.

taylor swift midnights john mayer
Taylor released a 3am edition of Midnights, featuring an emotional song about John Mayer. (Credit: Taylor Swift)

Call Her Daddy Podcast (2022)

Following the release of Midnights, John appeared on the Call Her Daddy podcast. During his interview, he shared more details about his dating life – though, he didn’t explicitly mention Taylor. 

“The elephant in the room is that I’m on a show that caters to women, and I have a couple of name plates on me like ‘lothario’ and ‘womanizer’,” the singer said. 

He went on to claim that people “would be surprised” to learn he is confused by the monikers.

John also expressed that he has a history of falling for people “very deeply”. And that he used to think that somebody showing interest in him was an “accident” he needed to “capitalise on.”

“Dating is no longer a codified activity for me, it doesn’t exist in a kind of… It’s not patterned anymore,” the Gravity singer said, explaining that sobriety played a big part in his decision.

john-mayer-call-her-daddy
John on Call Her Daddy. (Credit: Instagram)

Speak Now (Taylor’s Version) (2023)

If you’re new to the Swiftie fandom, here’s a crash course on the hit record

The updated version of Speak Now was released on July 7, 2023.

“I first made Speak Now, completely self-written, between the ages of 18 and 20. The songs that came from this time in my life were marked by their brutal honesty, unfiltered diaristic confessions and wild wistfulness,” Taylor said of the album.

“I love this album because it tells a tale of growing up, flailing, flying and crashing … and living to speak about it.”

Taylor-swift-performing-on-stage-in-a-pink-sparkly-ball-gown
Is Swift revisiting the Mayer relationship in her Eras Tour? (Credit: Getty)

Taylor Lautner speaks out on Speak Now (2023)

Lautner is actually married to a Swiftie – his wife’s name is also Taylor, making it the ultimate Tay-triangle. And one hell of a confusing topic to write about. So, we’ll be going with surnames for this one.

In May 2023, Lautner addressed the fact that his relationship with Swift would return to the spotlight thanks to the re-release of Speak Now. In particular, the song Back To December was written about their split. 

Speaking with TODAY, Lautner joked that he “feels safe” ahead of the release.

“I think it’s a great album. Yeah, I feel safe… Praying for John,” he joked.

The following day, he shared a TikTok video set to the song Dear John. He jokingly got on his hands and knees and prayed. We think it’s pretty clear he’s on the Swift side here.

taylor swift and taylor lautner speak now songs
Taylor & Taylor in their heyday. (Credit: Valentine’s Day)

How does Taylor Swift feel about John Mayer now? (2023)

Interestingly, there are no nods to Taylor’s relationship with Mayer in her Eras Tour set list… so far. In fact, Swifties are divided about only one song from Speak Now being on The Eras Tour set list: Enchanted.

Having said that, she is performing surprise songs at every show. For an acoustic portion of the set list, Tay is delving into her archive for an unscheduled number or two. So far, we’ve seen the likes of Tim McGrawState of Grace, and Exile.

During her Eras Tour in Minneapolis, Taylor shared that there were only 13 days left until Speak Now (Taylor’s Version) was released. And how did she celebrate it? By performing a rare live performance of Dear John – the first time the song had been sung live in more than a decade.

Before she sang the song she took a moment to ask fans not to cyberbully John Mayer…without mentioning his name of course. 

“I get to stand on the stage every single night of this tour and watch the most beautiful things happen,” she told the crowd. “Like, I watch you guys make friends with each other. I watch you bond. I watch you give each other friendship bracelets. I see so many beautiful interactions happen and I hear so many stories about friends that were made at these shows and I watch it happen every night. It’s the most unbelievable thing to watch.”

“And so, I was hoping to ask you that as we lead up to this album coming out, I would love for that kindness and that gentleness, to extend on to our Internet activities.”

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