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It’s widely known that Taylor Swift‘s award-winning songwriting has taken inspiration from her own life and relationships. That’s not to outweigh the fact that she often writes about the life experiences of others and creates intricate worlds and fantastical scenarios in her head as well, but for the sake of this timeline, we can focus on the first half. It’s also known that her fans, affectionately called Swifites, can often investigate and uncover who a song is about in seemingly no time at all. Taylor’s 10 studio albums have been written over the course of nearly 20 years, which has unavoidably taken fans through several of her relationships, from Joe Jonas to Joe Alwyn and beyond.
One relationship, however, has a hold over Swifties: 19-year-old Taylor’s months-long romance with fellow musician John Mayer, who was 32 when they were together. The romance is thought to have influenced several songs on her 2010 album Speak Now, whose re-recorded counterpart, Speak Now (Taylor’s Version), is dropping on July 7. Fans believe one track in particular, “Dear John”, speaks about Taylor’s regret over dating the talented guitarist. In the song, she laments over her older ex’s “dark, twisted games” and that she “should’ve known” better than to mess with him.
In honor of the release of the iconic Speak Now (Taylor’s Version), let’s dive into Taylor Swift and John Mayer’s relationship timeline.
Taylor Swift and John Mayer met in 2009 and were friendly through mid-2010 (Photo: David Fisher/John Salangsang/Shutterstock)
John Tweets That He Wants To Collab With Taylor
John made the first move — although it seemed platonic. In March 2009, he tweeted that he would love to collaborate with the “Love Story” hitmaker after getting a song idea stuck in his head. “Waking up to this song idea that won’t leave my head. 3 days straight now. That means it’s good enough to finish. It’s called Half of My Heart, and I want to sing it with Taylor Swift,” he tweeted, per Distractify. “She would make a killer Stevie Nicks in contrast to my Tom Petty of a song,” he added.
Taylor Invites John On Stage At Her Fearless Tour
Taylor caught wind of John’s admiration for her as an artist and invited him on stage during her Fearless tour two months later. The Los Angeles show marked their first performance together. They sang two songs: Taylor’s “White Horse” and John’s “Your Body Is a Wonderland”, according to PEOPLE.
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Taylor Says She Is A ‘Massive’ Fan Of John
Taylor Swift poses at the 2023 Grammys (Photo: David Fisher/Shutterstock)
In June 2009, teenage Taylor said John is at the top of her list of artists she’d like to collaborate with in the studio. “He Twittered the other day that he wrote a song and he wants to make it a duet with me. I freaked out when I heard, because I’ve been such a big fan of John for such a long time,” she gushed to Elle. “I’m really excited about just the idea that he would even mention me in his Twitter!”
Taylor And John’s Collaboration Is Born
Taylor and John’s dreams came true when they officially collaborated on “Half of My Heart”, which made his Battle Studies album. The album dropped on Nov. 19, 2009. While promoting the album, the “New Light” singer raved about working with the rising country star. “Taylor is the world’s biggest star who doesn’t know she’s a star. Which I think is totally sweet. 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,” he told Access Hollywood. “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.’”
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He added, “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.”
Weeks after his album was released, he gushed about Taylor once more during an appearance on The Ellen DeGeneres Show. “I’m a huge fan, and I think she’s got a really great voice,” he noted. “She’s one of the smartest, most talented people around right now. … I think she’s that genuine.”
Taylor And John Perform ‘Half Of My Heart’
John Mayer and Taylor Swift perform at Z100’s Jingle Ball in 2009 (Photo: Amanda Schwab/Starpix/Shutterstock)
Taylor and John took the stage together at the Z100 Jingle Ball in Dec. 2009, where they performed their collab. That same month, Taylor and Twilight actor Taylor Lautner had gone their separate ways. The following month, Tay and John were spotted grabbing dinner with some friends in Nashville.
John Presents Taylor With An Award
John and Taylor kept their relationship under wraps. The “Karma” singer was spotted at a taping for CMT’s Crossroads, which saw John perform, but they were not seen again until John honored Taylor at the Songwriters Hall of Fame Induction Ceremony in June 2010. “You could put her in a time machine in any era and she would have a hit record,” he said in his speech, which ended with him handing her the Hal David Starlight Award, per PEOPLE. “Don’t confuse everybody loving one thing as hype. Sometimes that’s everyone agreeing that it’s fabulous.”
Showing the most PDA ever in their relationship, Taylor sweetly kissed John on the cheek and hugged him as she accepted her award. That was the last time the pair would be seen on good terms.
Taylor Swift Releases ‘Dear John’
Taylor’s third studio album, Speak Now, debuted on Oct. 25, 2010. The fifth track on the album, “Dear John”, referenced a falling out when she was 19 years old — the age at which she dated the Dead & Company guitarist. “Don’t you think nineteen is too young/ To be played by your dark twisted games / When I loved you so?” she sang.
John Responds To ‘Dear John’
John Mayer famously dated Jessica Simpson in the early 2000s. Jessica has since spoken out about their toxic relationship. (Photo: John Salangsang/Shutterstock)
Fans assumed — and still do — that “Dear John” is about John Mayer, and so did he. In 2012, he said the song made him feel “terrible” while speaking to Rolling Stone. “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 complained.
John also said he was not happy about the lack of warning he received about the song that is potentially about him. “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,” he went on. “I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”
“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!’” he added.
Taylor Calls John ‘Presumptuous’
“How presumptuous,” Taylor said to Glamour in Sept. 2012 after John’s comments to Rolling Stone were mentioned. “I never disclose who my songs are about.” She also claimed she did not read exactly what he said about her. “I know it wasn’t good, so I don’t want to know,” she noted. “I put a high priority on staying happy, and I know what I can’t handle.”
“It’s not that I’m this egomaniac and I don’t want to hear anything negative, because I do keep myself in check,” the Pennsylvania native explained. “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.”
Taylor had already said she will never reveal the person behind a song in a 2010 interview with PEOPLE. “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,” the Grammy winner stated. “A lot of times they don’t push send.” Taylor said adding the song to the album was her version of “pushing send”.
Taylor Asks Fans To Be Nice To John Without Naming Him
Taylor Swift on the release of ‘Speak Now’ TV before performing ‘Dear John’:
“I’m 33 years old, I don’t care about anything that happened to me when I was 19… I’m not putting this album out so you can go on the internet and defend me against someone you think I wrote a song… pic.twitter.com/cFQbKQk8vD
— Pop Base (@PopBase) June 25, 2023
During her Minneapolis Eras Tour stop, Taylor asked fans to be nice to anyone they think her songs may be about before singing “Dear John” as a surprise song. Notably, it was the first time she had performed the song live since 2012. “I’m 33 years old. I don’t care about anything that happened to me when I was 19,” she noted, as seen in the above video. “I’m not putting [Speak Now (Taylor’s Version)] out so that you can go and 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.”
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Taylor Swift’s Eras Tour: International Dates, Surprise Songs, Full Setlist & More
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