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My High School Boyfriend Dumped Me Using Lyrics From Taylor Swift’s “Fifteen”

When I was 15, I was anything but fearless. That said, I blasted Taylor Swift’s album of the same name on an almost-daily basis, so today’s re-release of Fearless (Taylor’s Version) feels like my high school yearbook set to song. I have deep-seated memories tied to each and every track—but fond reflections aside, my cringiest and most devastating memory involves being quoted the lyrics of “Fifteen” during a break-up.

Yes, you read that right. I got dumped through a Taylor Swift song! Let’s set the scene, shall we? It was my freshman year and I had just turned 15 years old. I spent my days running around my Catholic high school in a plaid skirt and Ugg clogs with long, poorly-straightened hair. At night, I played guitar and convinced myself I had Taylor Swift-level singing talent (which, bless my heart, I did not). I was preparing for a small, local show when I met the soon-to-be love of my high school life. Let’s call him Stephen, in honor of Ms. Swift.

Stephen was a junior at my high school and a full-blown piano prodigy. He was tall and lanky with a smattering of acne scars across his cheeks and I was absolutely obsessed with him. He felt the same and we started dating, a move which my mother definitely did not co-sign. He was three years my senior, but I thought it was romantic! We were star-crossed lovers. No one could tell me otherwise.

STYLECASTER | Taylor Swift Fearless

I’ll skip the mundane details of our three-month relationship—we watched a lot of Scrubs, listened exclusively to Jack’s Mannequin and drove around in his Honda Accord—and fast-forward to the night where it all went to shit. As a freshman, I felt extremely cool to be able to attend Stephen’s junior prom. I bought a bubble-hemmed red Jessica McClintock dress and sparkly silver heels for the occasion.

The only problem? The heels were too big! I remember impulsively stapling the straps for a better fit moments before he picked me up at my house. We had already been having a little trouble in paradise (In truth, my depression had made me a pretty miserable person to be around) so I knew I couldn’t blow it by messing up our night at the prom.

However, it didn’t take long for the staples in the straps of my shoes to start digging into my ankles, causing some very minor bleeding. Embarrassed but eager for a chance to leave the dance floor (I was a freshman! I didn’t know a soul there besides Stephen!), I resigned myself to our assigned table and watched my boyfriend enjoy his night. I thought I was doing the right thing by letting him go on without me, but it would ultimately be my downfall.

STYLECASTER | Taylor Swift Fearless

Hours later, Stephen dropped me off at home instead of taking me to the after-prom party. He told me we’d talk in the morning and I knew I was screwed. By the next day, I had convinced myself I was overreacting, and I still had my prom hairdo and hoops on when he came over to call it off. I broke down in Broadway-level dramatics and then—ever a musician—he said something I’d never forget.

“I mean, when you’re 15 and someone tells you they love you, you’re gonna believe them.”

How could this boy think quoting a Taylor Swift song would lighten the mood of our traumatizing break-up? Was he insane?? Naturally, I continued to sob and he left soon after. Looking back, I’m sure he thought the reference was funny, a nod to something I cared about. At the time, though, I didn’t know what bothered me more: Getting dumped or the fact that he had ruined one of my very favorite songs.

STYLECASTER | Taylor Swift Fearless

More than ten years later, a relationship that meant the whole world to 15-year-old me is nothing but a distant, cringe-and-laughter-inducing memory. Now, Stephen is married—all of my exes are, ironically—and I haven’t thought about him in years. That is, I hadn’t until “Fifteen (Taylor’s Version)” reminded me of a time in my life when high school romance was enough to knock me entirely off my feet.

Back then, the song’s chorus hit me hardest because it was the part I related to the most. Now, a different line stands out: “I’ve found time can heal most anything, and you just might find who you’re supposed to be.” Thinking of Swift re-recording this lyric in 2020, reminiscing on how far she’s come, I find myself getting chills. If time had already begun healing her back in 2008, I can’t fathom how healed modern-day Swift must be. And in so many ways, I have been equally healed by time’s generous gift of perspective.

Fearless is an album about young Taylor Swift, but Fearless (Taylor’s Version) is an album about every single one of us who listened. Swift’s music is confessional poetry set to song, but at age 15, I heard the tracks and wondered who she wrote them about—now, they’re tied to names and faces from my own experiences.

But out of all the genuine life lessons I’ve learned since Fearless’ original release, I can’t help but stress one in particular to anyone reading: Do not dump someone using a Taylor Swift song.

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