I was once an adoring John Mayer fan, but now Taylor Swift's the artist I relate to more thanks to her throwback 'Dear John'

Headshot of Taylor Swift in front of a cutout of John Mayer playing guitar, on a pastel pink-purple gradient background overlaid with old photos of them together when they dated
Taylor Swift and John Mayer's brief 2009 relationship is still making waves today.Jeff Kravitz/Getty; Tim Mosenfelder/Getty; Kevin Mazur/Getty; Dimitrios Kambouris/Getty; Marianne Ayala/Insider
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"Still Not Over It" is an essay series unpacking pivotal pop culture moments of the 2010s that rarely, if ever, got the deep dive treatment they deserved.

The winter of 2021 saw me entering a full-blown spiral. As a pandemic-induced storm of depression and anxiety raged inside me, I desperately clung to musical nostalgia.

Among the artifacts I'd dug up was a burned CD from 2006, when Taylor Swift's angsty "I'd Lie" precisely captured my sweetheart years of high school. I also found VHS tape footage of my freshman year dance performance to John Mayer's 2003 "Clarity" (viewed by way of a trusty HDMI cable).

Noticing my growing affection for retro tech, my husband gifted me a record player along with a vinyl record of "Evermore." I was by no means a Swiftie, but we both understood the financial and cultural value of her pandemic albums on vinyl. I quickly fell in love with her newest masterful songwriting, pushing me to reconsider her other albums I'd glossed over.

A few days later, I rediscovered "Dear John," the 2010 break-up ballad from Swift's third studio album "Speak Now." Over revealing lyrics and a damning chorus, Swift recalls her toxic relationship with the megastar John Mayer, who collaborated with and dated the 19-year-old when he was 32.

Armed with my new affinity for Swift's literary stylings and fired up from recent reckonings of society's treatment of Britney Spears and other famous young women of the aughts, I pressed play. My mouth fell open when the opening thwangs of a guitar transported me to a time when my own 19-year-old self listened to Mayer's melancholic music on repeat. "'Dear John' sounds exactly like a John Mayer song," I realized.

I was stunned to hear not only the similar musical links between Swift's song and Mayer's discography but also the young singer's deft portrayal of what it's like to be manipulated by an older man. In the chorus, she sings a rhetorical question right at her target: "Don't you think I was too young to be messed with?" Further in, Swift describes tip-toeing around his volatility, "praying the floor won't fall through again."

The track has only become more lauded in Swift's discography while Mayer's hits soured as his objectifying, crass, and racist behavior and comments toward women made headlines. Even 13 years after its debut, "Dear John" still perfectly encapsulates the sliminess of Mayer and the lyrical and musical genius of Swift.

My love for teen pop stars like Swift and artists like Mayer clashed as I grew older

john mayer taylor swift
John Mayer and Taylor Swift performed together at Z100's Jingle Ball in 2009.Kevin Mazur/WireImage for Clear Channel Radio New York

"Dear John" was written by Swift sometime in late 2009 or early 2010, according to Swift's interviews about her "Speak Now" album. That means she penned the song right after we had both left our high school years behind. By then, years of trying to be a "cool girl" had distorted my music tastes. Too many boys I knew showed disdain at worst and boredom at best whenever I tried to share my love for popular, radio-dominating artists like Swift or Spears. And so I entered a self-hating phase where I scoffed at and rejected the talents of women who reminded me of myself, wrapping the most girlish parts of me in shame and tucking them away.

Mayer made the cut, though. Between his famous friendship with Dave Chapelle, his undeniable guitar skills, and him being a man and all, the guys in my life didn't hate on him as much. And thankfully so, because his songs seemed to interpret my depressive, self-loathing adolescent thoughts as beautiful enigmas.

His music was a genuine comfort to me, particularly when his debut album came out in 2001, the kickoff to my middle school matriculation. "Why Georgia," Mayer's 2001 hit and my favorite of his, played on repeat on my Walkman as I walked home alone from school. "Everybody's just a stranger but that's the danger in going my own way," he crooned with yearning. Later, when I moved to New York City at 18, I'd post this same lyric on my Facebook page. The words felt like freedom, a whole new life at my fingertips.

But now, 15 years later, that's what Swift's music does for me. In her most personal songs, Swift excavates her tarnished girlhood and details her evolving self-portrait in a way that feels incredibly close to my own journey into adulthood.

Rediscovering my love for Swift has given me the freedom to process a lot of recessed teenage memories

 

In a 2012 Rolling Stone cover story, Mayer described "Dear John" as "cheap songwriting" and an "abuse of talent."

"I'm pretty good at taking accountability now, and I never did anything to deserve that," Mayer said. "It was a really lousy thing for her to do." His criticisms are ironic, considering that he's also written songs about his famous exes, including one seemingly about Swift.

But when Rolling Stone asked Mayer about the song's line, "Don't you think I was too young to be messed with?" he simply stated, "I don't want to go into that.'' Mayer has refused to engage seriously on the topic of Swift's age at the time and the power dynamic between them having a 13-year age difference, which means he may not be as good at "taking accountability" as he may believe.

Throughout my late 20s and now early 30s, important conversations have emerged about power imbalances, age gaps, and abusive behavior that is rampant among high-profile celebrity men. A thread of that reckoning is the reevaluation of how famous young women were treated during their teen years or during publicly toxic scandals (Spears, Janet Jackson, and Pamela Anderson, to name just a few).

Growing up for me has been a constant evolution of self-perception, untangling years of shame, hubris, and resentments. I'm ashamed of the misogynist, anti-teen-girl rhetoric I once repeated to defend Mayer and dismiss Swift and her young female peers. Without realizing it at the time, I was mimicking patriarchal talking points that enable men like Mayer to publicly date a teenager in the first place.

But among the shame is a deep feeling of compassion for my younger self, who only ever wanted to listen to music she loved and dance and fit neatly into the world. Mayer's music once gave me a window to a happier future. Now Swift is speaking right to my present and past.

'Dear John' will always be a timeless classic tucked among Swift's wildly popular catalog

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Taylor Swift's album art for 2022's "Midnights."Beth Garrabrant

Swift is now 32 — the exact age Mayer was when they were romantically tied together. Her latest release, "Midnights (3am edition)," included a track called "Would've, Could've, Should've," which serves as a sequel to "Dear John."

Now an adult herself, Swift uses this song to expand on the regret and restlessness that comes with memories tied to a loss of innocence. The bridge of "Would've, Could've, Should've" peaks when Swift sings the final two lines with a girlish crack in her voice: "Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first."

That pleading line is both devastating and cathartic. My own memories flood back when I hear it: leers from grown men in their car while I ride my bike to grade school, a friend telling me she'd "gone all the way" with her high school boyfriend when she was barely 13, the first kiss forced upon me when I was 14, and so many other small moments that have buried themselves in my gut. How many more generations of young women will recognize the pain in Swifts's songs? Could vulnerable songwriting help stop the cycle?

Swift stood in the power of her girlhood when she was a teenager as best she could. Now she's a grown woman flexing her songwriting prowess and reclaiming agency. That healing is infectious, like an exfoliation of our collective shame from the aughts.

In the final line of "Dear John," Swift flips the responsibility back on Mayer: "You should've known."

Mayer should've known better. He should've known she was too young to be messed with. He should've known how to take accountability when the time came for it. It wasn't on us — the teen girls of the '00s — to know better. That's on the John Mayers of the world.

Read the original article on Insider