From hearing Teardrops on My Guitar at 15 to crying over her engagement at 33, Taylor’s songs have always found me right where I was.
I was fifteen the first time I heard Teardrops on My Guitar on the radio and while nobody around me really knew who Taylor Swift was yet, I kept listening anyway, even finding her on Myspace where I looped her songs over and over, feeling like I had stumbled upon something that felt like mine, something that made sense to me in ways I couldn’t quite explain yet, even if nobody else around me understood it.
Taylor’s post on Myspace accessed by a fan using Wayback Machine | Photo from Reddit
When Fearless came out in 2008, everything shifted because suddenly Taylor wasn’t just my little discovery anymore, she was everywhere, and Love Story was playing on every radio, blasting from mall speakers, sung at school fairs and dances, and for me, every track felt personal, like a parallel life, my first relationship lined up with that record. Full of insecurities and wanting to be chosen like in You Belong With Me, and then when I finally felt loved back, it was Fearless, it was those tiny moments that made everything else fade. By the time Speak Now (2010) came out, I felt steadier in myself, more anchored, and Mine became my anthem for what it felt like to hold on to some kind of security in love and in life.
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Then came Red in 2012, though at the time I didn’t realize just how much that album would mean to me later on. By 2014, 1989 had taken Taylor into full pop reinvention and for her, it was the start of a new chapter, but in my own life I was already somewhere else, preoccupied with my first real job and with a love I thought would end in the altar, so while the albums were there, I wasn’t living in them the way I once did, I was busy trying to hold together a version of adulthood that felt important at the time.
And then came 2016, the year everything fell apart, the year I got my heart broken and lost people I loved, the year my own world went silent at the exact same time that Taylor’s did too, because after the whirlwind of 1989 and the Kim-Kanye feud, she went on hiatus, no songs, no appearances, nothing to hold onto, and that absence felt heavy, so I turned back to Red and 1989 as if they had been waiting for me all along. Suddenly All Too Well wasn’t just a song, it was heartbreak word-per-word, The Moment I Knew echoed grief I didn’t know how to voice, Clean became a promise that maybe someday I’d come out of it, and in those months when everything felt gone, those records carried me through.
When Reputation finally arrived in 2017, it wasn’t just her comeback, it was mine too, because she embraced the snake and reclaimed her power, and I was doing the same in my own way, moving from EA to managing editor, landing my first big byline, meeting people who shaped the next part of my life, and every beat of that record felt like reclaiming my voice.
By 2019, Lover painted the world in pastels, and for Taylor, it was her most romantic album, while for me it was also the season when someone from my past resurfaced with apologies and promises of a second chance, and at 27 it was flattering, almost like a Wattpad story, almost like a storyline she might have written, but reality was harsher, because like You’re Losing Me, I realized I had already given too much, and eventually like Midnight Rain I let go, because I knew I was worth more than what was being offered, and at times it even felt like he pulled a Jake Gyllenhaal on me, “calling me back again just to break me like a promise.”
Then came the pandemic, and with it Folklore and Evermore in 2020, albums that arrived like lifelines, quiet but strong, full of characters and stories that felt like companions when I was quarantined at home, sick with COVID, while my tita, who was like a second mom to me, fought for her life in a hospital, and while my company struggled under pressure and my anxiety rose higher than ever, I clung to those records, finding myself in Mirrorball, feeling fragile and fractured but still shimmering when the light hit.
Her re-recordings from 2021 onward felt like a reset, not just for her but for me too, because while she was rewriting her past and reclaiming her voice, I was also starting again with a healthier job, rewriting my own habits after burnout, and reminding myself to prioritize my health.
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When she gave us the 10-minute version of All Too Well, I wasn’t the same person who had once cried through the original on loop, because this time I remembered everything vividly but with distance, the pain was still there but it didn’t own me anymore, and that song became less of a wound and more of a marker of who I had been.
Then came Midnights in 2022, and with it I made my circle smaller, unfollowed people who no longer belonged, returned to keeping a diary, keeping my moves quieter, just like she was doing, and when The Tortured Poets Department landed in 2024, I was at another breaking point, stuck in a job that mistreated me, humiliated me, until I finally walked away without a backup plan, terrified but free, reminding myself that like she sang, “I can do it with a broken heart.”
Her NYU speech replayed in my head as I pushed myself forward. Around this time, Taylor had also gone through her own ending—her split from Joe after six years—and while that loss echoed in her songs, there was also the beginning of something new with Travis. In a way, that mirrored my own life, reminding me that endings, no matter how heavy, can also clear space for what’s next.
By then, I had also missed her Eras Tour—even though I had tickets for Singapore, I couldn’t afford to go, and it felt like another heartbreak, but it also proved to me that this was never just fangirling, that her music had been more than concerts or merch, that it had been survival.
And then in 2025, she got engaged, and I cried like I was the one who had said yes, because after all these years, it felt like watching a friend get her happy ending, and in my own life I found a version of that too, a place that valued my voice, gave me space to grow, (Hi, The POST!)
The fifteen-year-old girl who first heard Teardrops on My Guitar is now thirty-three, still a work in progress, with, as Taylor once said in her documentary Miss Americana, a sharper pen, a thinner skin, and an open heart, and like her I’ve stopped people-pleasing, learned to keep my circle small, and focused on what really matters.
Being a Swiftie since 2007 means I’ve had a soundtrack for every heartbreak, every milestone, every loss, and every comeback, and while Taylor wrote the songs, they have become the chapters of my life too.
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