The 2010 song “Dear John” by a teenage Taylor Swift openly discussed her relationship with John Mayer, sparking a wave of reactions. This track became a pivotal point for many, including Renfro, who admits it prompted her to rethink her past dismissal of female pop artists.
WHILE YOU READ: Explore a playlist featuring songs by John Mayer and Taylor Swift.
“Still Not Over It,” a series of essays, delves into significant pop culture moments from the 2010s that merit deeper examination.
In the winter of 2021, a personal crisis unfolded. Battling pandemic-induced depression and anxiety, I sought refuge in the comforting embrace of musical nostalgia.
Among the relics unearthed was a burned CD from 2006, carrying Taylor Swift’s angst-ridden “I’d Lie,” a perfect soundtrack to my high school sweetheart years. VHS tapes also surfaced, capturing my awkward freshman dance performance set to John Mayer’s 2003 hit, “Clarity”—revisited through the magic of an HDMI cable.
Observing my growing fondness for vintage technology, my husband gifted me a record player, complete with Taylor Swift’s “Evermore” on vinyl. While not a die-hard “Swiftie,” I recognized the artistic and commercial significance of her pandemic-era vinyl releases. Swift’s masterful songwriting on “Evermore” captivated me, compelling a fresh listen to her albums previously overlooked.
Shortly after, “Dear John,” the poignant 2010 breakup anthem from Swift’s “Speak Now” album, resurfaced. With raw lyrics and a powerful chorus, Swift recounts a toxic relationship with John Mayer. Their collaboration and brief romance occurred when Swift was 19 and Mayer was 32, highlighting a significant age disparity.
Equipped with a newfound appreciation for Swift’s lyrical storytelling and energized by recent societal re-evaluations of the treatment of young female celebrities like Britney Spears, I pressed play. The opening guitar chords of “Dear John” instantly transported me back to my 19-year-old self, immersed in Mayer’s melancholic tunes. A striking realization hit: “‘Dear John’ sounds exactly like a John Mayer song.”
The similarities weren’t just musical. Swift’s song skillfully depicted the experience of being manipulated by an older man. The chorus posed a direct, rhetorical question: “Don’t you think I was too young to be messed with?” Further lyrics described navigating his unpredictable moods, “praying the floor won’t fall through again.”
“Dear John” has only ascended in Swift’s discography, while Mayer’s reputation has been tarnished by objectifying, insensitive, and racially charged behavior and remarks towards women, widely reported in the media. Even over a decade later, “Dear John” remains a potent encapsulation of Mayer’s questionable actions and Swift’s lyrical and musical brilliance.
The Clash Between Teenage Pop Love and Growing Up: Swift and Mayer
Image: Taylor Swift and John Mayer performing at Z100’s Jingle Ball in New York City, 2009, highlighting their professional collaboration before their personal relationship became public and controversial.
Swift penned “Dear John” around late 2009 or early 2010, as interviews about her “Speak Now” album reveal. This timing places the song’s creation just as my own high school years concluded. Years spent trying to embody the “cool girl” archetype had warped my musical preferences. Sharing my enthusiasm for mainstream female artists like Swift or Spears often met with disdain or indifference from male peers. Consequently, a self-deprecating phase emerged, marked by dismissing the talents of women who mirrored parts of myself, burying “girlish” inclinations in shame.
Mayer, however, escaped this dismissal. His association with Dave Chapelle, undeniable guitar skills, and simply being male, shielded him from the same critique. His music, thankfully, resonated deeply, seeming to transform my adolescent angst and self-doubt into something profound and beautiful.
His music offered genuine solace, particularly his 2001 debut album, released as I navigated the complexities of middle school. “Why Georgia,” his 2001 hit and personal favorite, was a constant companion on my Walkman during solitary walks home from school. “Everybody’s just a stranger but that’s the danger in going my own way,” he sang, capturing a sense of yearning. Later, at 18, moving to New York City, this lyric became a Facebook caption, embodying freedom and new beginnings.
Now, years later, Swift’s music evokes similar feelings. Her deeply personal songs unearth her own complicated girlhood and trace her evolving identity with remarkable resonance to my own journey into adulthood.
Reclaiming Teenage Memories Through Rediscovering Taylor Swift
In a 2012 Rolling Stone cover story, Mayer labeled “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 asserted. “It was a really lousy thing for her to do.” This criticism is ironic, considering Mayer’s own history of writing songs about famous exes, including one seemingly about Swift.
When Rolling Stone pressed Mayer about the lyric, “Don’t you think I was too young to be messed with?” he deflected, stating, “I don’t want to go into that.” Mayer’s consistent avoidance of directly addressing Swift’s age and the power imbalance of their 13-year age gap casts doubt on his claims of “taking accountability.”
Throughout my late twenties and early thirties, critical dialogues have emerged regarding power dynamics, age disparities, and abusive behaviors prevalent among prominent men in the celebrity sphere. A key aspect of this reckoning involves re-evaluating the treatment of young female celebrities during their formative years or during public scandals— figures like Spears, Janet Jackson, and Pamela Anderson come to mind.
Personal growth has been a continuous process of re-examining self-perception, disentangling layers of shame, arrogance, and resentment. Shame now accompanies the misogynistic, anti-teen-girl rhetoric I once echoed to defend Mayer and dismiss Swift and her female contemporaries. Unknowingly, I was perpetuating patriarchal viewpoints that normalize older men dating teenagers.
Yet, amidst the shame, a profound compassion emerges for my younger self, who simply sought to enjoy music and belong. Mayer’s music once offered a glimpse of a brighter future. Now, Swift’s music speaks directly to my present and past.
“Dear John”: A Timeless Classic in Taylor Swift’s Repertoire
Image: Taylor Swift’s “Midnights” album art, released in 2022, representing her continued evolution as a songwriter and artist, now reflecting on past experiences with mature perspective.
Swift, now 32—Mayer’s age during their relationship—released “Midnights (3am edition)” in 2022. This album includes “Would’ve, Could’ve, Should’ve,” a song functioning as a sequel to “Dear John,” offering further reflection on the past relationship.
As an adult, Swift uses “Would’ve, Could’ve, Should’ve” to explore the lingering regret and unease associated with lost innocence. The song’s bridge culminates with Swift’s voice cracking with emotion as she sings, “Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first.“
This poignant line is both heartbreaking and liberating. It triggers a cascade of personal memories: unwanted attention from older men as a young girl, a friend’s story of sexual experience at a young age, an unwelcome first kiss at 14, and countless subtle moments buried deep within. How many more generations of young women will find resonance in Swift’s candid songwriting? Can such vulnerable music help break cycles of harmful behavior?
Teenage Swift stood in her youthful power as best she could. Adult Swift now wields her songwriting prowess, reclaiming her narrative. This healing process is contagious, like a collective shedding of the shame accumulated from the early 2000s.
In the final line of “Dear John,” Swift shifts the responsibility back to Mayer: “You should’ve known.“
Mayer should have known better. He should have recognized she was too young to be manipulated. He should have learned to take responsibility. The burden of knowing better wasn’t on us—the teenage girls of the 2000s. It rested squarely on the shoulders of figures like John Mayer.
