How long did Taylor Swift Date John Mayer?

As Swifties know, we’re currently living in 2021 (Taylor’s Version). The brilliant, often ruthless, songwriter we know as Taylor Alison Swift is unleashing emotional chaos with one album launch after another as she re-records her masters.

After releasing her folklore and evermore albums last year, Taylor revealed she would be dropping the new versions of her old albums in order to claim ownership of her masters. So far, she’s released Fearless and Red, plunging us all into the emotional turmoil of our teen years and early 20s heartbreak.

With the recent release of Red and the 10-minute version of All Too Well, Taylor fans have been reliving joy of her pop-country sound. Not to mention, the good old days of listening to her break-up tracks about Mr 'Steal Your Scarf' himself, Jake Gyllenhaal.

Still to come, of course, will be the Taylor's Version of Taylor Swift, Speak Now, 1989, and Reputation. In particular, Speak Now will be responsible for causing us to have an emotional breakdown. The album was entirely written by Taylor when she was just 19, and features soul-destroying tracks about her famous exes Joe Jonas, Taylor Lautner and John Mayer.

While Joe is already in on the joke – he’s friends with Taylor, and his wife, Sophie Turner, poked fun at the Fearless release earlier this year – exes like John might not be ready for it. 

If you weren't aware of this particularly juicy moment in pop culture history you might be wondering, did Taylor Swift and John Mayer really date? Yes! Taylor and John dated briefly between 2009 and 2010, when she was 19 and he was 32. A sore point that scored its own famous, heartbreaking lyric in the aptly named song Dear John.

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. Though, it’s fair to say most people come out on Team Swift in this debate. So, let's go back to the beginning...

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The Tweets (2009)

John first reached out to Taylor on Twitter in March, 2009, which was apparently the only way he could contact her for some reason. John tweeted about wanting to record a song with the Fearless singer, comparing her to Fleetwood Mac icon 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 starstruck 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 a subsequent 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.

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, stepping out to sing Your Body Is A Wonderland and White Horse with Taylor.

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

Considering how things unfolded between these two, the lyrics to Half of My Heart were quite fitting. 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, the pair 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.

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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 have been reports that the pair split ways around February 2010 – but that would make it QUITE strange for John to have presented Taylor with an award in June of that year.

Considering how she felt about their split, we don’t know that they would have been hugging and sharing kind words about one another if they had broken up at this stage. But then again, Hollywood is all about the behind-the-scenes drama.

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. If they had already split at that point, it seems something must have soured after this event.

"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,” he said of Taylor in his speech, leading many to believe they were still together.

The Songwriters awards took place shortly after the CMT Awards, which both stars attended. At the time news outlets reported they had been there together. Many believe that another Speak Now song, The Story of Us, is about their encounter at that award's show – where Taylor tells the story of an on-off romance coming to an end and sings about being in a "crowded room" but not speaking to one another.

A few months later, in October, Taylor would use her songwriting prowess to detail their eventual split in excruciating detail when she released a song about their relationship called Dear John.

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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 from the album. 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.”

Interestingly, when Taylor performed the song in concert on her Speak Now tour, she wore a very similar dress to the one she was wearing when John presented her with the Songwriters award.

As Swifties know, Taylor never does anything accidentally. Aside from being a deeper shade, the cut and style of the dress - and how she styled her hair - were way too familiar to be coincidental.

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The Fallout (2012)

Some fans may not remember, but a few years after Dear John was released John did something very few of Taylor's exes have done: he spoke out about the song. The star claimed it was unfair for her to release it. The quotes recently resurfaced, after John spoke out about the treatment of women in Hollywood. 

Earlier this year in 2021, John spoke about the Framing Britney Spears documentary, with many fans taking the opportunity to point out some of his past mistakes with exes like Taylor and Jessica Simpson. Namely, how he contributed to the ongoing narrative about Taylor being “boy obsessed” and “crazy” for writing songs about her relationships. Something he does regularly.

Part of his large contribution to the “woe is me, a woman wrote a song about me” brigade came via a 2012 interview with Rolling Stone. John complained about his ex and said Dear John is “cheap songwriting” and that he “didn’t deserve” to be called out by Taylor.

"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 songwriting," 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 songwriting of his own on Paper Doll.

Paper Doll (2013)

In his track Paper Doll, John details an ex who he “was good to” and puts the blame of the split back onto the girl who was “a little paper doll” and 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.

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The Birthday Tweet (2016)

In 2016, four years after John said Taylor’s song was cheap, he out of the blue decided to hit send on a tweet that was accused of being rather shady. But, he claims it was innocent and went on to delete it.

On Taylor’s 27th 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.”

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, since she was hardly going to respond.

During a Q&A and performance 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.”

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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 famously allowed Shawn Mendes to collaborate with her on a duet remix of her smash hit. For some reason, Shawn decided to do an Instagram Live with John, where the latter mocked her songwriting on the track Lover. Cool move, Shawn! What an absolute bro vibe, bro!

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."

In a word: Awkward.

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Speak Now (Taylor's Version)

The updated version of Speak Now - and likely vault tracks to be released about John - have not yet been dropped. But if the response to Red regarding Jake Gyllenhaal is anything to go by, fans will be having a field day. Big yikes! 

Tina Burke

Tina Burke is the Digital Lead for WHO, obsessed with all things pop culture, entertainment and lifestyle. When she’s not writing about the latest TV shows, you’ll find her aimlessly scrolling through TikTok.