• Nineteen Magazine

Re-evaluating Taylor Swift And Jonn Mayer's Relationship 11 Years Later

This blog post is written by guest author Shannon McNamara of Fluently Foward. (Which is a super cool blog about love, dating, and other interesting topics every millenial will love.)


Of all of Taylor Swift’s highly publicized relationships, her relationship with John Mayer has been the one that fascinated me the most.

Image: https://www.pinterest.com/instyle/


Most Swifties know the general facts about their relationship: they dated briefly in 2009, had a falling out, and the result was an infamous song titled Dear John on Taylor’s album Speak Now.


The song had incredibly moving lyrics like “I lived in your chess game, but you changed the rules every day,” and “don't you think nineteen is too young to be played by your dark twisted games,” that led people to believe what we had always suspected: John Mayer is a douche.

At the time when John and Taylor dated, he had a reputation as Hollywood’s resident bad boy. He had dated Jennifer Aniston - and had a very public breakup - as well as Jessica Simpson, and gotten serious grief for referring to Jessica Simpson after their breakup as “sexual napalm in bed,” which led people to be even more curious that Taylor Swift was associating with him. What was Hollywood’s sweetheart doing with someone like that?


And as Taylor points out in Dear John as well, there was a serious age gap of 12 years between them - she was 19 while he was 31. Their relationship seemed to be that of mentor/mentee at first since they started getting close when Taylor sang on John Mayer’s track Half of My Heart. Rumors circulated of course, of the two dating, but it wasn’t until the release of Dear John that a relationship was confirmed.


As a loyal Swiftie, I always found their relationship intriguing. I assumed through the lyrics of Dear John that they had a relationship that was too mature for Taylor at the time, and toxic by the hands of John, and Taylor probably fell into a phase of puppy love with him that he didn’t reciprocate - most likely because he’s emotionally unavailable. (Or at least, that was my working theory)


But then I stumbled upon this YouTube video.

It’s eight minutes and 34 seconds of John Mayer complimenting Taylor Swift and commenting on her nature on a variety of interviews that happened around the time they dated. I probably watch this video once a year and it gives me serotonin. I’m not even the girl John is talking about in these clips, but hearing him describe Taylor in this manner makes me completely sure of the fact that there was something very serious between them.


Here are some of my favorite quotes from the video.

  • They only make a few Taylor Swift’s every decade

  • She’s just this...strange in all the most beautiful ways, just doesn’t really belong to this universe type person

  • This woman is ageless

  • She’s just an angel, she’s like a pixie

And it puts my working theory to shame. Obviously their relationship didn’t pan out, and from the lyrics of Dear John we can assume that John was the one who held the power in their relationship...but when you listen to these quotes, it’s easy to tell that John was enamored by Taylor.

Image: https://www.pinterest.com/cristina181185/


Another interesting piece to their relationship was how John Mayer received the song Dear John. In an interview with Rolling Stone, he was asked about the song and said he felt “humiliated” from it, “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.”


And when he was asked specifically about the controversial lyric, “Don’t you think I was too young to be messed with?” he responded with “I don’t want to go into that.” Personally, I find that a bit suspicious.


The saga between them didn’t end there, though. In 2013, John Mayer wrote his version of Dear John - a song directed towards Taylor Swift called Paper Doll.


There were lyrics in there that tied Taylor to the song, such as “you’re like 22 girls in one” which referenced her hit song 22, and “someone’s gonna paint you another sky” which referenced her Dear John lyric of “you paint me a blue sky.”

In my personal opinion though, it wasn’t nearly as scathing as Dear John, and if anything, was kind of flattering. Maybe I’m nuts, but knowing a guy was so hung up on me that he wrote a song years after...it would be a total ego boost.


You might think that that’s all to the saga of John and Taylor, but I briefly want to touch on something that I really think not enough people have talked about. We know about the epic feud between Taylor Swift and Katy Perry, but what most people don’t talk about is how John Mayer and Katy Perry dated after he dated Taylor Swift.

I understand that Hollywood is a small enough place for this to happen, but when I hear about how their “bad blood” feud was the result of a business deal gone wrong with dancers on tour, I can’t help but think that those articles are missing another point.


John Mayer was obviously an impactful person on Taylor’s life at a young age, it seems (allegedly) like they had a passionate relationship where John ran circles around Taylor with mind games...and then cut to a few years later, and he’s on the Ellen show with Katy Perry as boyfriend-of-the-year, wearing a dorky Christmas sweater and being the monogamous man that Taylor probably thought he never would (or could) be. They even had a song together and made a...pretty cringey music video for it.


I’m not saying that Taylor and Katy were petty enough to have this cause their feud (after all, Taylor dated Joe Jonas and he dated her friend Gigi Hadid after) but I could definitely see it adding fuel to the fire.


It seems now like Taylor is happy with her current boyfriend Joe Alwyn, and John Mayer is...probably seeing multiple girls and doing drugs at home or something, but it will be interesting to see if these two ever find their way into each other’s lives again.


Let me know what your thoughts are in the comments below, and if you want to read any more of my content (about love and dating, New York City, and unpopular opinions) check out my blog FluentlyForward.

Cool Related Content You'll Love:

5 Reasons Why Taylor Swift and Harry Styles Would Have Been Perfect Together

Ranking Taylor Swift's 8 Albums

folklore Inspired Wallpaper


AND DON'T FORGET TO ENTER THE ULTIMATE TAYLOR SWIFT MERCH GIVEAWAY!!!


#taylorswift #johnmayer #celebrityrelationships

Nineteen is the premier blog for today's new adults. Established in 2020, Nineteen strives to provide you with the hottest stories to curb your curiosity. Keep reading for more on entertainment, celebs, and college content.

©2020 by 19.