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Taylor Swift singing in front of strands of pink lights in her video for her song Lover.
Image via Google Images

The music icon has endured a long road, filled with hits and heartbreaks, to find her soon-to-be husband.

Through Taylor Swift’s impeccable storytelling abilities, she’s mastered the art of entangling millions of adoring fans in her heartstrings, both when they’re strong and soaring and when they’re broken on the floor. She has immortalized her biggest losses of love with dramatic hair flips, soul-shattering bridges fortified with a lyrical infrastructure only she could build, and even a short film. Even the ones that got away never make it far from Swift, who has encapsulated her pain in some of the best breakup songs of the last decade.

However, where there’s a low point there’s also the euphoria of a new beginning. That fleeting feeling of falling for someone new is an emotion that she also manages to capture detail for detail. And while Swift has never explicitly disclosed the names behind the inspirations for some of her biggest hits, it seems that for the foreseeable future, there will only be one muse she has in mind. After dating for nearly five years, it seems that Swift and British actor Joe Alwyn have decided to agree that “all’s well that ends well to end up with you”.

But to reach this happy moment, there’s been a lot of “guitar string scars” that Swift’s had to endure. With the power of her pen and piano, she made it out and brought us along for the ride.

Let’s take a look at the hardest heartbreaks — and greatest hits — that led her to her “Lover.”

2006 – “Picture to Burn

Coming in red hot on her self-titled debut album, Swift’s dramatically pyrotechnic revenge anthem is reminiscent of Carrie Underwood’s “Before He Cheats” or even Dolly Parton’s “Jolene” — if they were set in the thralls of high school drama. Opening with banjos blaring, Swift sings triumphantly about her plot to “strike a match on all [her] wasted time” and how her “daddy’s gonna show [them] how sorry [they’ll] be.” She taunts, thrashing her trademark blonde curls, “nothing’s stopping me from going out with all your best friends” — and there’s no doubt that she means it. This angst-driven proclamation in the name of teenage heartbreak is still an absolute head-banger even over a decade later, a hallmark of early 2000s country music that sealed Swift’s fate as a lyricist early on in her career.

 

2008 – “Love Story

The lead single off her Grammy Award-winning sophomore album “Fearless” and probably the song that marked Swift’s true rise to stardom, “Love Story” is a touching modern tribute to the tragedy of Romeo and Juliet — but with an ending that even Shakespeare couldn’t muster. Spinning together themes such as forbidden love and destiny, Swift weaves a classic and unforgettable narrative that soars in the hearts of listeners, all in under four minutes. However, the true shining moment that remains even 13 years after its release is the final verse and chorus. With the star-crossed lovers’ romance potentially doomed, the cathartic build-up leading up to the lyrics is a scene straight from a fairytale: “He knelt to the ground and pulled out a ring / And said, “Marry me, Juliet / You’ll never have to be alone / I love you and that’s all I really know / I talked to your dad, go pick out a white dress / It’s a love story, baby, just say, ‘yes.’” Hopefully, Alwyn took a few cues from this touching tribute to young love when keeping happily-ever-after in mind.

 

2008 – “White Horse

Also featured on “Fearless,” this fifth track about the rebirth and growth that comes after love lets you down juxtaposes with that fairytale feeling Swift is able to capture so well. Perhaps even a melancholy echo to “Love Story” with the lyrics “I’m not a princess / this ain’t a fairytale / I’m the one you’ll sweep off her feet lead her up a stairwell,” she settles into the quiet resignation that comes with heartbreak. However, despite that simmering pain, by the end of the song, that refrain has changed. Swift stands up confidently saying, “I’m gonna find someone someday who might actually treat me well” and provokes her lost lover to “try and catch [her] now.” If 18-year-old Taylor could see her now, I think it’s safe to say she would be quite pleased with how the scenario played out.

 

2010 – “Dear John

Perhaps Swift’s most candid breakup ballad to date, this hard-hitting saga of a toxic relationship is a cult-classic favorite with Swifties everywhere. While of course Swift never explicitly names the subjects of her songs, she spells it out for us pretty plainly over the course of this almost seven-minute track. John Mayer, who Swift dated when she was 19 and he was 32, is most likely the muse inspiring the iconic lyrics: “You are an expert at sorry, And keeping the lines blurry / Never impressed by me acing your tests / All the girls that you’ve run dry / Have tired, lifeless eyes / ‘Cause you burned them out / But I took your matches before fire could catch me / So don’t look now, I’m shining like fireworks over your sad, empty town.” And, before you ask, in true Swift fashion, they came with real ones.

 

2010 – “Enchanted

Working with the whimsical and fairytale feeling of her third album, “Speak Now,” Swift crafts the euphoric rush of meeting someone new and the highs that come with infatuation. Using her natural storytelling abilities, she sets a scene of someone who is unhappy with their life, full of “walls of insincerity, shifting eyes and vacancy” — all things that melt away when they catch a glimpse of this magical person, leaving them “blushin’ all the way home” and staying up until 3 a.m. fantasizing, praying “please don’t be in love with someone else.” The duality that Swift captures in this windswept ballad made for romantics everywhere is simply a standout addition to her lyrical legacy.

 

2012 – “All Too Well

Hardcore Swifties and casual fans of Swift’s catalog will inevitably agree that this heart-wrenching ballad that captures the confusion and desperation after a breakup is one of her all-time best. That being said, it’s no surprise that Rolling Stone named it No. 69 on its Top 500 Songs of All Time list. It features some of her best lyrical work to date — even the original 10-minute draft released this past fall – with sharp-cutting confessions of loss. The part that hits the closest and promises to leave its listeners breathless and broken, however, comes with the bridge: “And you call me up again just to break me like a promise / So casually cruel in the name of being honest / I’m a crumpled up piece of paper lying here / ‘Cause I remember it all, all, all / Too well.” Such bold declarations of heartbreak backed up with Swift’s tear-stained vocals make such a song about loss utterly unforgettable, haunting its listeners over a decade after its initial release.

 

2014 – “You Are in Love

This bonus track on the deluxe version of “1989” is an emotional and intimate portrait of love in its purest forms. Listeners catch images of burnt toast on a Sunday morning with a lover, the quiet domesticity and joy that comes in a flourishing relationship. Swift, who has “spent [her] whole life trying to put [love] into words” does just that with this stripped-back reverb-y dreamscape of a song. The lyrics, which are relatively simple compared to her other work, illustrate the contentedness that comes with a partner that makes you feel complete, the repeated “you are in love, true love” a mantra to romantics everywhere.

 

2017- “Call It What You Want

After the 2016 leaked phone call between her and Kanye West, Swift promptly disappeared from the public eye. Upon her return almost 18 months later, it seemed that she had found not just peace in her isolation, but a new romance too. Reportedly meeting each other at the 2016 Met Gala, Alwyn and Swift began officially dating during her hiatus, and when she came back into the spotlight, she wielded her explosive and razor-sharp seventh studio album, “reputation.” However, while the opening tracks bleed with anger and plots of revenge for the way the media had treated her, Swift’s storytelling eventually gives way to the power of love and “starry eyes sparking up [the] darkest nights.” This intimate portrait of a love that can double as protection in a time where everything seems hopeless grants it a spot as one of her best love songs to date.

 

2019 – “Lover

In the upper echelons of Swift’s songwriting catalog, you’ll find this soft-spoken letter to her lover — Alwyn. Despite wanting to keep their relationship away from the prying eyes of the media, Swift invites her listeners into their world that’s filled with Christmas lights in January and a home where they make all the rules. Tinged with anxiety, believing such a love is too good to be true, she confesses to worries like “everyone who sees you wants you,” making it raw and extremely relatable. Coupled with a bridge that’s reminiscent of a wedding march and vocals that tremble with tenderness, this dreamy ballad immortalizes the love that Swift has yearned for all of these years and, finally, has.

 

2020 – “Invisible String

On the stripped-back “folklore,” which earned Swift her third album of the year award at last year’s Grammys, she speaks candidly about how funny fate can be. Reminiscing on her past with the opening lyrics, “Green was the color of the grass where I used to read at Centennial Park / I used to think I would meet somebody there,” she stages the timeline for the unraveling of her love life, bringing her to the very moment where she ends up with Alwyn who, “pulled [her] out of all the wrong arms,” wrapping her “past mistakes in barbed wire.” The philosophical pondering that this song inspires, starting with the simple “one single thread of gold tied me to you,” is a hopeful beacon to its listeners. In the end, following over a decade’s worth of heartbreak and loss, it’s safe to say that she’s found her forever friend and lover.

Writer Profile

Maggie Habermas

University of Texas at San Antonio
English

Aspiring to be a professional sad girl that writes about music, movies and books that make me feel.

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