Since Valentine’s Day is tomorrow, it’s the perfect time to listen to Taylor Swift’s most soul-crushing breakup songs to ever grace this earth.
- loml– The Tortured Poets Department
The deceptive song title stands for “loss of my life,” not to be confused with “love of my life.” This harrowing song reflects on an all-consuming love that once felt everlasting, bringing you back to life only to leave you pleading for what’s left of yours in the end. Like the rest of “The Tortured Poets Department”, every single lyric in this song is pure poetry.
“When your impressionist paintings of Heaven turned out to be fakes. Well, you took me to hell too. And all at once, the ink bleeds. A con man sells a fool a get-love-quick scheme.” These gut-wrenching lyrics clearly come straight from Swift’s diary but manage to put words to an experience millions have suffered through.
- Better Man– Red (Taylor’s Version) and Little Big Town’s The Breaker
Originally written for the “Red” album but scrapped and given to Little Big Town, this song took on a new life when Swift finally released her version on “Red (Taylor’s Version).” “Better Man” tells the story of missing a toxic former lover even after all they put you through. You know you deserve better and that’s why you left, but you still can’t help but wish they’d change.
“But your jealousy, oh, I can hear it now. Talking down to me like I’ll always be around. Push my love away like it was some kind of loaded gun. Oh, you never thought I’d run.” The emotion behind every single lyric in this song, combined with the rawness that the acoustic guitar provides, will strike you down every time.
- Would’ve, Could’ve, Should’ve– Midnights (3am Edition)
A powerful follow-up to “Dear John”, detailing the pain and anger that follows being taken advantage of at a young age by an older man. The memory of what they did to you haunts you and continues to grow more sour the older you get. Waking up at 3 a.m. pleading for your innocence back, hurting for that version of yourself. Thinking about what you would’ve, could’ve and should’ve done differently.
“If clarity’s in death, then why won’t this die? Years of tearing down our banners. You and I. Living for the thrill of hitting you where it hurts. Give me back my girlhood. It was mine first.” Swift depicts the trauma response of begging to erase the past, hoping that your abuser hurts. There’s a considerable amount of pain one must go through before they turn from completely loving someone to hoping they’re out there somewhere bruised.
- You’re Not Sorry– Fearless and Fearless (Taylor’s Version)
The oldest song on this list, reminiscent of one’s first heartbreak. The evocative lyrics capture the feeling of a betrayal so deep that it completely destroys the version of them you fell in love with. You’re done waiting for them to come around because you’ve realized they’re not the person you imagined them as.
“You had me crawling for you, honey and it never would’ve gone away, no. You used to shine so bright but I watched all of it fade.” The medley of “Back To December/Apologize/You’re Not Sorry” from the “Speak Now World Tour” takes the song to a whole new level of sorrow.
- How Did It End?– The Tortured Poets Department: The Anthology
Last and most certainly not least, the nauseating masterpiece that is “How Did It End?” Swift perfectly encapsulates the utter agony one physically feels after a serious relationship comes to an end, again. Reeling as you attempt to make sense of what caused the relationship to fail. Bracing for impact as those around you badger for answers and share their unwelcome opinions.
“Say it once again with feeling. How the death rattle breathing. Silenced as the soul was leaving. The deflation of our dreaming. Leaving me bereft and reeling. My beloved ghost and me. Sitting in a tree. D-Y-I-N-G.” A timeless piece of poetry that leaves you with new emotional scars even after the 1,000th listen.
