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  • Kaitlyn Nicole

Top 13 Saddest Taylor Swift Breakup Songs


Taylor Swift The Tortured Poets Department Sad Break Up Songs Promotion Picture Vinyl Album Cover
Photographer: Beth Garrabrant

It's no secret that Taylor Swift is one of the best lyricists of our time, if not all time. She's able to be poetic and intelligent, while also staying highly emotional and relatable which is why she is loved by so many. It's also no secret that a topic she happens to write about that hits the hardest to many in her fanbase are the breakup songs. There's something about the way Taylor Swift can describe emotions that the average person couldn't possibly do. Taylor uses her words and her voice to speak for others and to say what others fail to say which is why so many people feel like her songs are about them. Taylor has plenty of sad break up songs, but the ones on this list are the ones I find to be the most devastating and gut-wrenching. Especially with her latest album, The Tortured Poets Department, Taylor was able to add songs to her discography that may just be some of the saddest songs I've ever heard. And yes - don't worry - these are all Taylor's Version.


If you're looking for the saddest Taylor Swift songs that are unrelated to break ups, read our Top 10 Taylor Swift Songs That Will Make You Cry article!


13. Forever & Always (Piano Version)


There's something about the piano version of Taylor's song "Forever & Always" from the Fearless album that just hits different. The original version of the songs feels angry, while this version gives it more of what comes after the anger stage is over - the deep sadness, confusion, and grieving. The way Taylor sings softer and with more falsetto, even changing some of the rhythm in the melody at times to make it sound more like she's speaking adds to the emotion. You can hear her gasping for air as if she's about to cry while recording and it leaves a pain in your chest. I also love how she changes the bridge to be like how she would preform the song way back on the Fearless tour.



12. I Almost Do


This is just my personal opinion, but I believe "I Almost Do" is one of Taylor Swift's most underrated songs. Some of the lyrics in this song really hurt, especially if you've ever experienced a relationship like this where you knew it wasn't good for you so you literally had to force yourself to stay away from them. Lyrics like, "I bet it never ever occurred to you, that I can't say hello to you and risk another goodbye" are the reason why this song made it on this list - along with the fact that it sounds like belongs in a romantic drama movie.




11. Say Don't Go


Whenever 1989 (Taylor's Version) first came out, "Say Don't Go" instantly became my favorite vault track. My jaw was on the floor while reading the lyrics, hearing the hauntingly beautiful vocal harmonies and the iconic, Out of the Woods esque production. The dead silent pause after the bridge finishes when Taylor sings "why'd you have to make me love you? I said I love you.. you say nothing back" is enough to physically take anyone's breath away just out of absolute shock. It's so hard when you give somebody your all just for them to act like what you had meant nothing.




10. Better Man


When Red (Taylor's Version) came out, everyone was so excited that we finally got to hear Taylor sing "Better Man", which didn't make it on the original version of the album and was given to Little Big Town by Taylor because she felt it was too good of a song not to share still (which she was right). Although Little Big Town did an amazing job making this song their own, Taylor brings a whole new level to the emotion and meaning behind this song in her own recording. There's nothing harder than trying to get over someone that could've been the one, if only they had cared or tried a little more.




9. Dear John


There's a lot of anger and pain in the song "Dear John", and I think that's what makes it so sad. The imagery in this song is so vivid, you can put yourself in Taylor's shoes. It also hits even harder once you realize how young she was when she wrote this song. She way way too wise beyond her years at this point, but she didn't deserve what she had gone through. Although it's a really rough song to listen to, it's also very empowering at the same time as she doesn't hold back ripping this man a new one and exposing exactly who he is and what he had done to her. Now let's remember, this song is over a decade old and Taylor has reminded her fans that she is over things like this; these songs are now ours to use as our own.




8. How Did It End?


Come one, come all, it's happening again. "How Did It End?" is one of the tracks on The Tortured Poets Department: The Anthology and to me, is one of Taylor's most poetic songs to date. I mean, the bridge is literal poetry mastery between the words, rhymes and rhythms that make you feel like you're listening to a poem being read to you. "How Did It End?" is about how people don't know how to leave someone alone when they're going through a breakup. They want to get in your business and know all the details rather than giving you the space and privacy you need to heal. There are a lot of lyrics in this song that are tear jerking, like "and so a touch that was my birthright became foreign" and "guess who we ran into at the shops? walking in circles like she was lost. Didn't you hear, they called it all off. One gasp and then, how did it end?" - but probably the most painful moment is one many can agree on, at the end of the bridge when Taylor sings "my beloved ghost and me, sitting in a tree, D-Y-I-N-G".




7. The Black Dog


On my first listen of The Tortured Poets Department, "The Black Dog" was the one song that made me burst in to tears by the time it was over. This song is so undeniably tragic and emotional. The pain behind Taylor's voice is the strongest I've ever heard out of any other song from her. The bridge is probably one of the most relatable bridges Taylor has ever written and is exactly how most people feel whenever they go through a devastating break up. The part that catches you the most, is the break in her voice at the very end of the song. If you've heard it before, you know exactly what I mean.




6. Champagne Problems


Whenever the Evermore album came out, "Champagne Problems" collectively became a fan favorite song. The song is about being proposed to, but not being ready to take that next step; so you end up breaking their heart when you have to turn them down. This song also is one of Taylor's best bridges of all time which is why fans love it so much. It's builds with such intensity and emotion, and it's filled with words. Of course we can't forget the moment she sings "she would've made such a lovely bridge, what a shame she's fucked in the head, they said." We need more "I'm the problem" songs when it comes to relationships ending, and this is a great one.




5. loml


You'd assume at first glance that "loml", off of The Tortured Poets Department would stand for "love of my life" - in fact, Taylor tries to trick us throughout the song that it is what it stand for up until the very last line when we find out it actually stands for "loss of my life". This stunningly heartbreaking piano ballad is no doubt one of the saddest songs I've ever heard in my life. It's about falling so deeply in love with someone who ended up not caring about you at all and they just left you to drown in your own tears. There's really no other way to explain it, you just have to listen.




4. The Smallest Man Who Ever Lived


"The Smallest Man Who Ever Lived" is another one of those "Dear John" situations where the tone is more angry than it is sad, but the emotions are just so high and intense that listening to it makes you feel sad and heartbroken for anyone who has had to go through something like this (or if you have yourself). This song ends on one of the biggest bridges Taylor has ever written, both lyrically and dynamically. The lyrics that get me the most in this song are "You deserve prison but you won't get time" and "you are what you did, and I'll forget you but I'll never forgive the smallest man who ever lived".




3. So Long, London


"So Long, London" is a song where every single line is just gut punch after gut punch after gut punch. Anyone that I've seen react to this song would say "oof" after every single line they heard. Even though Taylor doesn't like when people speculate who her songs are about, it's pretty clear who this one is about - and you can hear just how much this relationship had affected her by the end. She was past the point of giving up, and was holding on to something that would never be brought back to life. It's really hard leaving a long-term relationship even after you've lost feelings because you're just so used to having that person in your life and you don't want to feel like you've wasted years on something for nothing.




2. You're Losing Me


I see "You're Losing Me" as the prequel to "So Long, London". It's when you're debating whether the relationship is worth still fighting for or not; you're not numb to it yet, and there is still some love left there. The song starts with a devastating sigh, and you know right then that this song is going to tear you apart. This song was released as a vault track from Midnights after the announcement of Taylor's 6 year relationship coming to an end. This was Taylors way of giving just a little bit of insight of what she had been going through.




1. All Too Well (10 Minute Version)


This probably comes to no surprise, but not only is "All Too Well" one of Taylor Swift's best break up songs, but it's also one of her best songs ever of all time. Especially when we're talking about the 10 minute version, this song dives deep into this universe and story that is so descriptive and heartbreaking beyond words. If you're a swiftie and you've never cried while singing "and then you call me up again just to break me like a promise, so casually cruel in the name of being honest" then you'd be lying.



What did you think of our list? What is your favorite break up song by Taylor Swift? Was there a sadder one you felt deserved to be on this list but it wasn't? Follow us on our socials below and let us know your thoughts!


Written By Kaitlyn Nicole



*copyright not intended. Fair use act, section 107.


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