With the recent release of The Tortured Poets Department, I figured it was time to roll out the red carpet with Episode 4 of the Taylor Swift Archives! This one is going to be a fun (and controversial) one.
Taylor is quick to brandish her sword of feminism if anyone brings up her past lovers. "Nobody says that about Ed Sheeran, and nobody says that about Bruno Mars," she once famously argued. "They're all writing songs about their exes, their love lives, and nobody raises a red flag there." As with most things, she's partially right -- Taylor Swift becoming the national lightning rod for slut shaming in the early 2010s was pure misogyny, and the way women everywhere piled onto the bandwagon to happily hate on her is honestly sad. But this doesn't change the fact that her success and Girl-Next-Door image is, in no small part, attributable to the way she has invited speculation and conversation regarding her personal life for the past twenty years of her career.
So yes, we're going to talk about her boyfriends. But I'm a raging feminist, so let me make one disclaimer: the rest of this blog post will be about Taylor Swift the character, not the person. I'm interested in these relationships from a purely literary standpoint, as I think each one is presented in such a trope-heavy way it's practically akin to reading fanfiction. But we must remember two key facts: 1. no matter how close our para-social relationships get, we actually know nothing about any of these random celebrities, and 2. if you find yourself emotionally invested in the relationship or reputation of a stranger, you should log off the internet and take a walk.
That aside, let's get started!
Chapter 1: The High School Love
Early Taylor Swift was vicious: in her debut album, she croons about a boy named Drew in Teardrops On My Guitar and later confesses how she hopes Cory will "stay beautiful". In the liner lyric notes for Should've Said No, she capitalized the letters S, A, and M every time they appeared, not unlike the way her recent song "thanK you aIMee" is not-so-subtly directed towards Kim Kardashian. It's the most brash and brazen she has ever been in revealing the true subjects of her masterpieces, but frankly, these relationships were too private and low profile for anyone to investigate these accusations at the time.
As far as we know, Taylor's young loves were just that -- so very high school. Yet, over the years, they've become the physical representation of the life she could've had: a "postcard" of a "picture perfect shiny family" coming around every holiday season, a boy who only remembers her when she's "on TV". In Midnight Rain she laments all the hearts she broke while chasing fame, and in tis the damn season she fantasizes about driving from her old school to her parents' house in the truck of a boy she once knew.
Much of the early critiques Taylor received was that she played the victim too often -- her music is always deeply proud, so sure she's right and she's been wronged. Perhaps her usual self-righteousness is what makes these quiet confessions of regret so heartbreaking. In many ways, this is the closest she'll come to wishing for another life. In The Prophecy off her most recent album, she begs for a way out of what she deems to be her destiny -- unquantifiable wealth, but no one to sit on the porch with at 89.
But the other reason this subgenre of Taylor's catalog is so precious to fans is the same reason Robert Frost's poem about roads diverging still brings a tear to my mother's eye. We've all made choices at the "young and stupid" ages that we come to regret at the "old and wise" ones. We all remember the first boy we ever had a crush on, and sometimes still hope to run into an old flame when shopping with our parents in our home towns. It's the idea of possibility, that we could rewind the clock and find a better path forward, that lingers -- could Taylor have stayed in Redding, Pennsylvania, and still found fame? Is there a way to have it all, the way we thought we undoubtedly would at fifteen? These are the questions these songs ask.
Chapter 2: The Bad Boys
Next, Taylor entered the public sphere. She exposed Joe Jonas on Ellen's talk show, and wrote scathing tracks about the coming apart of her relationship with Taylor Lautner, but ultimately the only real difference between them and Cory is that they was famous. It would be the relationships after that marked a distinctive break from the milquetoast accessories she had been carrying around: namely, John Mayer and Jake Gyllenhaal.
At the time, these relationships were the first "adult" experiences Taylor had -- she met Jake's sister, and allegedly defied her father to stay with John Mayer. Gyllenhaal introduced her to high-brow society, and John Mayer was a musical hero of hers far before they started dating. Perhaps because of this, the coming apart of these relationships seemed to change her in a molecular way -- she was moved to tears every night singing All Too Well on the Red tour, and her voice breaks on the studio recording of Dear John. Listening to her more recent reflections on these relationships -- namely, Would've Could've Should've or The Manuscript -- reveals how traumatized and scarred she truly was in the wake of these breakups, and how she put herself back together by sleeping in her mother's bed for months on end.
In the narrative of Character Taylor's life, these relationships mark the deconstruction of several themes and values that previously colored her perspective on love. She seemed to step away from ideas of fate and destiny, removing religious language almost entirely from her songs for several years. For albums afterwards, she'd write about love like a game or winnable prize, which is in stark contrast to the "pure" and Shakespearean way she thought before.
It goes without saying that these songs are important to fans who have similar experiences with older, manipulative men. But these songs are widely regarded as some of the best in her career, trauma aside. Why? Because transformation is deeply relatable. This kind of dramatic paradigm shift -- frequently at the hands of malicious, older people we're simply desperate to impress -- is a keystone experience in coming of age. Simply put, this loss and eventual reclamation of girlhood is so personal and private; but Taylor, with her keenly observant lyrics, proves that it's something we all feel in the exact same way, and this universality disarms us.
Chapter 3: American Dynasty
To those of you who aren't chronically online, you might not know that Taylor Swift dated Connor Kennedy (yes, that Kennedy) before the release of her album Red. It was a short-lived, relatively uncomplicated relationship with an amicable breakup, but something about the relationship -- and who Taylor became during it -- has always fascinated me. During it, she wore knee-length, A-line skirts for an entire summer, dressing like a middle-aged woman at the ripe age of twenty-two. She spoke with an air of opulence and class, and wrote about Bobby and Ethel Kennedy's timeless love story in Starlight.
What is interesting here is not that Taylor used her relationship as material for songs. It's not even that she changed her image quite dramatically to (presumably) fit within what the Kennedys deemed appropriate. What's surprising is her fixation -- then and now -- with the idea of an American monarchy, and the almost scientific way she sought the closest thing to it she could find: the Kennedy family.
Her obsession with the Kennedys has its reasons: if she had married into their family, she would be even more ubiquitous than she is now, dominating conversations about music, culture, film, entertainment, production, direction, and politics. In an almost Gatsby-ian twist, she'd hold both her own wealth (new money) and the Kennedy riches (old money) simultaneously, shifting between the popstar aesthetic she has now, and one of quiet luxury. It would've been an incredible power move, because even if Connor Kennedy remains irrelevant, the Kennedys as a family business do not -- one just has to look at Robert F. Kennedy's presidential bid to see that.
The song I associate with this chapter isn't even about Connor at all -- it's the last great american dynasty. This song is about the history of her house, and how her relationship to it ties her irrevocably to the mad, dramatic, vilified Rebekah Harkness who owned it before her. With this song, I've always imagined Taylor standing triumphant. Perhaps her original plan to marry into a dynasty didn't work out (after all, Taylor is too much of a romantic to stay in a loveless relationship for the sake of an idea), but turns out she didn't even need the boy at all. She did it herself.
And as a girl whose Plan B (if this whole "get a job" thing doesn't work out) is to marry rich, I can't help but admire her immensely for it.
Chapter 4: The One That Got Away
For those of you on the internet in 2012, I'm sure you remember how earth-shattering the New Year's Kiss between Harry Styles and Taylor Swift was. And their subsequent park date (with Taylor's publicist and her toddler). And the following album 1989, revealing that Harry Styles does have a fatal flaw after all -- he can't drive.
Jokes aside, the Taylor-Harry relationship was, at that time, her highest-profile one to date. Obsessed fangirls were angry she was living their fantasy. They escaped to private ski resorts with Ed Sheeran and wined-and-dined at bars and after parties with Paul McCartney. In 2014, Taylor was preoccupied with seeming cool and mature, and Harry Styles was just the coolest. As she talks about in Suburban Legends, he wasn't sophisticated like Connor, and therefore he wasn't the route to winning the favor of 'serious' critics. But he was immensely popular, a songwriter himself, and someone that she probably related to and aspired to be in equal measure.
Taylor Swift once said about Harry Styles that he's the love of hers that could "interrupt [her] wedding screaming 'we're not done yet!'". This trope -- of a relationship with no closure, just clues left in songs to each other for over a decade -- is fascinating. Of course there are pointed attacks at him and his yacht -- Style and Is It Over Now? come to mind. But far more interesting are the ones she's written years later, from the removed perspective of an indifferent woman. In the 1, she simply states that "it would've been fun / if you would've been the one", and in Question...? she wonders aloud if he thinks about their tumultuous, anxiety-ridden relationship, acknowledging that their current situations are probably more "suitable and nice". She, like most of us about that one boy who simply ran too soon, is gripped by the idea that he stays up each night pacing, wondering if they should give their love another chance.
And even more curiously, she often gets a response. From interviews and unreleased leaked tracks like Him, to songs written for other artists (I Love You) and himself (Perfect, Two Ghosts), Harry and Taylor have been having a very public conversation through lyrics and whispers, musing thoughtfully on their short-lived relationship for years now. It's not dissimilar to watching Sleepless in Seattle, admiring from a distance as two people bear their souls for our entertainment.
Chapter 5: True Love
There was a brief messy period separating Harry and this next chapter -- she dated Calvin Harris, who she has frankly refused to mention since. She was also briefly linked to Tom Hiddleston, predicting a pattern of clinging to whoever is closest when everything is crumbling around her that she would later replicate with Matty Healy in 2023. But the next official chapter is regarding her longest relationship yet: Joe Alwyn.
Alwyn was a departure from her usual romantic pursuits for a variety of reasons. He was unfamous and private, preferring to hide out in London instead of capitalize off the fame that comes with dating the world's biggest superstar. He was intellectual and high-brow, giving Taylor the approval from art critics and tortured poets that she had craved her entire career. We knew nothing of their relationship besides the blurry candid shots we received of them walking down various streets, but every song released about their relationship was achingly romantic. Taylor loves rewriting history -- in the months since calling off their relationship, she has recategorized many of the songs off reputation and Lover as "in denial", going so far as to pretend some of them were actually inspired by fictional stories instead of real-life events. Her fans have jumped on this bandwagon: is "you don't ever say too much" a compliment or insult? Is it really a good thing to have a partner whose "integrity makes [you] feel small"? But the truth is this: these are some of the most romantic songs ever written, and Joe served a very important purpose both in terms of romantic tropes that characterize her writing and also in her own personal and career narrative.
Let's start with tropes: this is the true love, the one who convinces you that love isn't volatile or mercurial, but "golden" and peaceful. This is the boy who you become so familiar with, you start calling his mother 'Mom'. Once they broke up, Joe became the poster boy for what my sister calls "bare minimum effort men" -- i.e., men who are perfectly content with everything remaining the same for all eternity, who are scared of the real commitment of marriage/children, who make you question if you're settling or just bored, who, once you finally leave, realize kept you from fully breathing. (To revisit the disclaimer: I don't know if these characterizations are fair or accurate and frankly, I don't care. This is the literary trope that Taylor leaned on to represent Joe in song, not a commentary on the quality of the person themselves.)
For Taylor herself, Joe was the man in her corner during the most transformative period of her life. She met him during her lowest low -- when her career was crumbling around her, she was suicidal, and went into hiding for an entire calendar year. During this time, she clung to him like a lifeboat, moving in with him and escaping the clutches of fame entirely. Then, as she began rebuilding her career, she used Joe to preemptively deter criticism -- the tired, common insults of "she's just writing about her exes" didn't apply when she was happily in love, and by not parading her relationships around or causing drama amongst A-Listers, she was finally able to win respect from her detractors.
Once the harshest lockdown regulations began to lift, however, Taylor began plotting towards reclaiming her title as the master of pop. Most fans theorize that this is when Taylor and Joe's relationship began falling apart, but frankly, I'd be willing to bet these underlying currents of tension had caused a lot more volatility within the relationship that we, as fans, simply weren't privy to while it was happening. If Taylor's life was a movie or book, this would absolutely be the end, but unfortunately, reality does not wrap narrative arcs up with neat little bows as often as we'd like. So as quietly as it begun, her relationship with the "love of her life" came to a close, and we moved on to her current relationship: Travis Kelce.
Chapter 6: American Pie
Her relationship with Travis Kelce was honestly quite inconvenient for my blogpost. I struggled to figure out which rom-com trope hadn't already been checked off, seeing as we had covered all the important bases. As I watched Taylor cheer Travis on at the Superbowl, however, I realized how short-sighted I was being; Trav doesn't just check off one trope, but two.
The first is the High School Power Couple. In Drew and Cory, Taylor has the high school love that she thinks about well into her thirties, but given that she wasn't the stereotypical popular cheerleader as a teenager, she never had the opportunity to be one half of an It Couple. In fact, despite her long history of dating ultra-famous men, she's never received the widespread adoration the way Ryan Reynolds and Blake Lively or John Krasinski and Emily Blunt have. Instead, cynics are usually jealous and vitriolic, and fans are protective and quick to anger. It's probably rare for Taylor to date someone who frequently makes her proud -- I'd wager it's usually the other way around. But as Taylor attended game after game, proudly sung that "karma is the guy on the Chiefs", and included stills of her successful, golden retriever boyfriend for TikTok, I realized that with Travis, she finally gets to bask in the glory of knowing she's on top of the mountain, and not alone.
But secondly, and arguably more interestingly, Kelce marks a return for Taylor to her all-American girl image. After years of dating "London Boys", Taylor's newest relationship is the most quintessentially American thing around: football and Thanksgiving, trading friendship bracelets and playing arenas. It's a callback to the earlier days where she sought out American dynasties to join, but this time, she sits on the throne as the matriarch and mastermind. Perhaps this is why fans are convinced that Travis is a perfect match for her; he's the amalgamation of tropes from eras past, confirmation that we are walking towards something even as it feels like we're running on a hamster wheel. Fans have loved finding accidental easter eggs in their love story -- Taylor's song The Archer matches up with Travis Kelce's touchdown dance, and Kelce's jersey number is 87, a number Taylor referenced in her debut album's Mary's Song. Coincidences like these remind fans that love, even though it so frequently fails, has the power to surprise us.
I'm reminded of Taylor's thesis from You Are In Love: "you understand now why they lost their minds and fought the wars, and why I've spent my whole life trying to put it into words". This love is more than romantic; it's triumphant. She's proving everyone who thought she was incapable of lasting in love wrong -- even herself.
Conclusion!
I'm well aware that most of this intense dissection of Taylor's relationships don't matter to the vast majority of people. However, I didn't just write six chapters on Taylor's exes for fun. (I mean I did, but there was another purpose, too.) I wrote it to demonstrate how she has managed to boil every single one of these relationships down to a singular thesis, a trope that can be summarized with a pithy catchphrase. In reality, these relationships were obviously more complex, but as a master storyteller, Taylor relies on well-worn images we all recognize and relate to. These men are fundamentally characters in the story of Taylor Swift, mostly serving to complement the reputation she so carefully curates for herself. One YouTuber I love, the Swiftologist, often refers to these men as "purses" -- the things she carries on her arm for a few paparazzi walks, but ultimately nothing more than a weapon to wield while mastering her craft.
And yet, these tropes are ultimately why her fans are loyal to the bone. No matter which stage of romance we find ourselves in, no matter which awful boyfriend we're currently in the midst of getting over, Taylor has a song for us that perfectly encapsulates our emotions (and make us the main characters in the process!). Perhaps Taylor has made a career off of these men, but make no mistake: the men are not why Taylor has a career.
Another interesting thing to note here is that as the chapters progress, the tropes become less about the men and more about Taylor. This is a key feature of her personal narrative -- that as she has aged, her growth can be measured by how she conducts herself in and after relationships.
But well, that's a story for another day.
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