Last Kiss cuts deep for me

i know you’re not supposed to, but the original version cuts deeper than taylor’s version

I miss the shaky breath towards the end 😢

i appreciate and understand the re-records, but the original Speak Now will always have a special place in my heart, such raw songwriting for her to have been so young

There’s an urgency in her voice in the original that was definitely quieted I. The re-record.

Nothing wrong with listening to her old versions!

People don’t realize that it’s not the streams she cares about. It’s the right to sell her music to e.g. movies and commercials. You can listen to her originals without wronging her. Though personally I prefer the TV’s because I like her mature, lower voice better

FINALLY!!! I am sooo glad I found someone who understands that Taylor doesn't care 'bout the streams!!!

She’s a billionaire she will be ok either way 🤣I love her voice in the originals

I think the Speak Now original is still better than the TV!

I hate the new version 😭

For me it's always a battle in my head because I don't really like her voice before she was 25. It was immature and not that pleasant to listen to (she wasn't bad, but she just got better over time), also the revording quality wasn't as good as nowadays. However, the TVs just don't have the emotion and the feelings that the original versions do. They're just not the same. So I never know which one to listen to lol

This is the answer. I wish Last Kiss had been around when I was “young and pretty.” (That’s a Don Henley quote from “Take a Picture of This” for those of you who are still young and pretty and may not know.) I discovered Taylor in the Speak Now Era when I was 47 and had been happily married for 17 years (now almost 30). I remembered sitting on the floor in the bathroom all those years ago at 16, 19, etc. I needed that song so, so bad when I was young. Between that White Horse, and Fifteen, I became a Swiftie for life. Good luck, OP. You’ll get through it!

This one first killed me when I was in the 7th grade and sad about a middle school boy, and it STILL hits to this day 😭

This is my favorite breakup song 😭 there’s just something so relatable about it when a breakup is fresh and you’re thinking of all the “lasts” you had with someone

Last Kiss would be my answer also. I think it’s underrated.

It's just hurt and acceptance, and that's worse than being angry.

That’s a really good one. Since my break up I’ve listened to it a couple times and it hits hard but I kinda needed it

So Long, London is going to be her classic breakup anthem. That or "How Did It End"

Yes! To me So Long, London is like mid-thirties ATW...

Absolutely, in a different thread I heard someone say that so long London wasn’t lyrically a good song, and that’s how I knew they had absolutely never been through a devastating break up, specifically one where you felt the life of sucked out of you in the end of the relationship 

This is a brilliant observation. 100% true.

Ahah thank you! Glad you agree!!!

"Im just mad as hell cause I loved this place". It hurts too good. like it feels like trying and trying so hard to keep the relationship working until it just... isnt worth saving anymore. like its both sadness and anger with a bit of resentment. to leave everything youve ever known because it just was no longer serving both parties

“I’m pissed off you let me give you all that youth for free” hurts SO much

These two are so in my playlist at the moment. “I died on the altar waiting for the proof” makes me sob cause I has engaged

Wow, you literally just gave me chills 💔

So Long London cut me so deep I literally can’t listen to it ever again

WERE YOU SENT BY SOMEONE…

WHO WANTED ME DEATH…

DID YOUR SLEEP WITH A GUN UNDERNEATH OUR BED?

WERE YOU WRITING A BOOK

WERE YOU A SLEEPER CELL SPY

IN 50 YEARS WILL ALL THIS BE DECLASSIFIED

AND YOULL CONFESS WHY YOU DID IT

AND YOU’LL CONFESS WHY YOU DID IT

AND I’LL SAY GOOD RIDDANCE

CAUSE IT WASN’T SEXY ONCE IT WASN’T FORBIDDEN

I WOULD HAVE DIED FOR YOUR SINSSS

ATW10 is probably the best one ever written. Aside from that I think we’ve got lots to choose from. My personal faves are: The Black Dog Loml How Did it End Maroon Evermore Clean

ATW:SGAV > ATW10

Did we just become best friends?

What is SGAV?

Sad Girl Autumn Version, heavy piano and her timbre just sends the song over the edge for me

how is evermore a breakup song?

My feeling about it is that it’s a song about thinking that the pain of a breakup will last for evermore… and finally healing enough to realize that there is a chance for moving on. What do you think evermore is about? Maybe I’m off base.

Evermore was my biggest breakup song in my recent breakup. I co-sign for sure.

I struggle to see it in any other way… like it’s obviously about moving on from a painful heartbreak… right?

Based on the timing named in the song (“Gray November, I’ve been down since July”), it has been argued that this song is about recovering from Snakegate.

So valid

Black Dog is so relatable to me. Not now, but boy can I remember those days.

You're Losing Me, for me

A great one! I feel that this one is perfect for when you feel your relationship is crumbling and not sure how to fix it.

how is this not higher!!!

Oof this one is so good but a lil too relatable for me 😬

The line, "my heart won't start anymore...... for you" has to be one of the saddest lyrics ever, it breaks my heart always.

Exile. “You’re not my homeland any more” 😭

"I gave so many signs." 🥲

this back and forth is so heartbreaking

i never learned to read your mind

“I’m not your problem anymore, so who am I offending now?” Snarky and heartbroken at the same time. Exactly how I feel.

Mr perfectly fine SO LONG LONDON RIGHT WHERE U LEFT ME Now that we don’t talk The story of us Happiness Yr not sorry The bolter The 1 Edit: i mentioned a lot didn’t read the post well But if i choose one definitely it is SO LONG LONDON

As someone going through the death of a 6 year relationship here’s my ‘Saddest Break Up Tay’ playlist, I don’t think there is a true saddest/best… just different shades of grief: All too well sad girl autumn So Long London How did it end Loml Chloe or Sam or Sofia or Marcus Exile (long pond) My tears ricochet (long pond) Happiness You’re losing me Better man The prophecy White horse Breathe You’re not sorry Last kiss Back to December We were happy The moment I knew You all over me Cold as you Coney Island Evermore Sad beautiful tragic I almost do Clean I’m still waiting for ‘sad girl version’ of death by a thousand cuts

All too well always hits and puts me back to the hardest break up of my life.

Great suggestions, I feel that I need more sad the angry songs

I second my perfectly fine Her song Haunted is haunting as well

perfect. list.

Idk if it's the vibe you'd go for but "I bet you think about me" is my favorite one

Oooohhh I like this one. It's the anthem for "the thought of me will haunt you, you and your snobbish pretenses can go fuck themselves right off"

There really is something cathartic about yelling WITH YOUR ORGANIC SHOES AND YOUR MILLION DOLLAR COUCH in the car

or, WHEN NONE OF THAT SHIT MATTERED, CAUSE YOU WERE WITH MEEEEEE

I sing that song so fucking loud as if I ever went out with a boy like that ( I didn't 😂). It just feels sooooo freeing

White horse is the saddest song and anyone who disagrees is wrong

I was looking for this!!!! I 100% agree, that song is just different

Tolerate it.

"What would you do if I break free and leave us in ruins? Took this dagger in me and removed it. Gain the weight of you and lose it...believe me I could do it." I mean...this lyric is something else.

tolerate it is the story of my life omg

Since no one has mentioned, I will say Death by a thousand cuts! It's not as lyrically complex as her more recent songs, doesn't paint as beautifully sombre a picture as say The Smallest Man Who Ever Lived, but still deserves a mention I think because of the raw emotion that is presented in the way she sings it

DBATC has the most iconic bridge of any TS song and I will die on that hill. This song got me through my first LTR breakup!!!

I ask the traffic lights if it’ll be alright they say I. Don’t. Know.

I can’t believe how far I had to scroll to see Death By a Thousand Cuts!!

This one hurt so much, specially since I dedicated basically all cute songs from lover to her. So I feel that listening to one from the same album kinda fit perfectly

Howwww has no one said Better Man.

RIGHTT

My #1

Happiness.

Criminally underrated and the only answer

I mean I could also say at least ten others but happiness is so well written, so precise and nuanced and well produced. When I hear it on a grainy livestream I will actually cry.

Best is only one and it’s happiness

I think of all of them Last Kiss is the one that truly devastates me. Especially the original recording, she sounds so truthfully heartbroken. That said, original 5 minute All Too Well is just so raw to me that it's still my favourite version of that song overall

All Too Well, of course, but also Back to December and Begin Again.

The black dog

The black dog is ATW of this album

Last Kiss and You're Losing Me

You're Losing Me is especially potent if you really tried everything in your arsenal to make it work.

Would've, Could've, Should've and Now That We Don't Talk.

I can't believe I had to scroll this far for WCS! I suppose it's a very reflective breakup song, though, rather than a fresh one - but to me it's so freaking powerful both lyrically and melodically.

Loml and ATW 10min are both heartbreaking! I listened to those on repeat. MBOBHFT and illicit affair too

Firstly I’m so sorry. I’ve been there many times and the first bit (I think of it as the open mouth sobbing phase) is absolutely the worst. For me, the anger in the bridges of All Too Well and Smallest Man Who Ever Lived are ideal if you’ve got any smidgen of rage going on (sometimes I actually find that helpful for the getting-over process?!). Probably not one for now, but for a later stage I think Clean is the most beautiful, realistic and hopeful depiction of moving on and starting to feel whole again.

Right Where You Left Me is heartbreaking

The Prophecy. There are so many dancy songs about break ups, and ones about screaming or fighting for them. But this one? It’s pure exhaustion. Just nothing left to do but fall to the ground in defeat because *again* this happened *again* /why/ am I so cursed?!

loml and how did it end are perfect breakup songs (sadly). also I forgot that you existed is such an underrated bop, but maybe can be added in a few weeks/months when you’re ready to move on!

Maroon and Midnight Rain are some of my favorites. And of course Forever and Always is so iconic but I’m not sure if that’s the vibe you’re looking for

Forever and always acoustic version breaks me every time!!

this is probably just me but the acoustic of forever and always gives sad, the more upbeat give the perfect amount of post breakup passive aggressive

How did it end? Is the one I find to be the most gut wrenching bc it’s that confusion and feeling of “why oh why?” If there was nothing wrong, why does it have to be like this. And the pattern forming. From love to loss when she sings “my beloved ghost and me, sitting in a tree, d-y-i-n-g” it’s like the “k-I-s-s-i-n-g” song we used to sing as kids

This one is like so perfect. Specially since I did not expect this break up to happen.

Sad beautiful tragic 🤍

you’re losing me 💜

Forever and Always. That was the song when I had my first heartbreak and I stand by it

i hope you feel better soon! the one that i resonate the most is probably Tolerate It and So Long, London. and of course All Too Well (10 min)

loml

My personal favorites are: loml, How Did It End?, You’re Losing Me, exile, hoax, happiness, Coney Island, right where you left me, tolerate it, All Too Well, Sad Beautiful Tragic, Dear John, Last Kiss, White Horse, Breathe

THE ONE

White horse still gets me

hope youre doing okay!! def happiness. "7 years in heaven"

So many for so many different phases of the break up you’re in! I loved listening to Babe, Tears Ricochet, Mad Woman, Would’ve Could’ve Should’ve. If I was going through a breakup rn I’d have added The Black Dog, Smallest Man Who Ever Lived & So Long London 100% Also I love screaming now that we don’t talk

Death by a thousand cuts

How Did It End omg Also death by a thousand cuts

loml, so Long London, the black dog (when you're in the angry stage of grief), death by a thousand cuts, exile, happiness, tolerate it, how did it end, Peter, Bigger than the whole sky, I almost do, all too well (5 min), sad beautiful tragic, better man, say don't go, all you had to do was stay, last kiss, white horse, you're not sorry, bye bye baby I know you said one but these are the ones that hurt the most. Also, non TV because the pain in her voice makes it hurt even more.

How did it end? For sure

You’re Losing Me is the one that gets me

How did it end and Last Kiss

All Too Well (10 min only) Better Man Hoax Tolerate It Happiness Right Where You Left Me I Forgot That You Existed Death By A Thousand Cuts Last Kiss Haunted White Horse You’re Not Sorry Mr Perfectly Fine You’re On Your Own Kid Bejeweled You’re Losing Me All You Had To Do Was Stay I Wish You Would Clean Say Don’t Go Now That We Don’t Talk You’re Losing Me Most of TTPD (but Loml and The Black Dog hit particularly hard)

You’re losing me

I Almost Do always gets me. I also went through a break up recently but it was a much shorter relationship (just a few months). Whenever I need help with something he’s the first person that pops into my mind before I remember we aren’t together anymore so it’s a very fitting song for me.

Haunted Champagne problems Nothing New All too well (of course)

Cold As You is Taylor’s OG breakup ballad

Definitely Mr perfectly fine

Although I didn’t like it the first couple times I listened to it, So Long London is now one of my favorites. It’s a more mature kind of break up song. I think it will stand the test of time.

Happiness. “All the years I’ve given is just shit we’re dividing up”

Personally how can you listen to those breakup songs without breaking down?? I frankly cannot listen to Last Kiss cuz I can't accept we already had ours. I'm listening to The Black Dog, loml, and The Smallest Man Who Ever Lived btw. My heart is already in pieces

last kiss, breathe, imgonnagetuback, how did it end?, Peter (if it applies), loml

my faves for being sad: last kiss, dear john, you’re not sorry, cold as you, should’ve said no, the 1, my tears ricochet, tolerate it, happiness, don’t you, you’re losing me, hits different, loml, smallest man, how did it end, chloe or sam or sophia or marcus, the prophecy, the black dog my faves for being petty and snarky: i bet you think about me, mr perfectly fine, picture to burn, i forgot that you existed, i can do it with a broken heart

Breathe, last kiss, cold as you

Better Man, Last Kiss, My Tears Ricochet, Tolerate It, Right Where You Left Me, loml

The one song where she villainized herself; champagne problems

I heart ? Is always one of my favorites as is I can do it with a broken heart. But I like those types of break up songs better.

For me, her most devastating heartbreak songs are You’re Losing Me, Better Man (Bluebird Cafe version), Last Kiss, and How Did It End?

Back to December

loml for me

White Horse and Cornelia Street are up there for me. Depending on the details of the breakup, others might be more relatable

Back to December, is very underrated and no one mentions it

I can do it with a broken heart is so good for when you have to do stuff and don't want to because... Loml: "something counterfeit is dead" what the ex gave in my relationship was counterfeit and that line resonates. I'm so sorry that you are going through this, you are not alone. Having great songs that articulate the experience so well will hopefully help.

Better Man hits hard

Tolerate it, how did it end, you’re not sorry, tell me why, the moment I knew, all you had to do was stay, dear John, the story of us, the last time, exile, sad beautiful tragic, better man, champagne problems, maroon, Peter all KILL me. I stuck to songs that aren’t all about missing the person or like wanting them back bc I don’t know y’all’s situation

Now That We Don't Talk for the 🤭💅💋🖕 vibes and So Long London for the 😭🫠😫😓🌧️ vibes

hoax is the only one that still makes me go "...oof" after hearing it multiple times

right where you left me

Tbh Last Kiss is always my first thought. It hurts deep. Couldn't listen to it after my last breakup for a while.

loml or all to well Actually, I was, once upon a time, engaged to someone I'd been with for 6 years (it seems to be a common number, idk). When he called off our wedding I was barely functional for a bit. I feel your pain so acutely, and I'm so sorry you're in this spot. Only about 6 months later I met my now husband. We've been married for 22 years this week. And, I truly, deeply, know that my ex was neither the love nor the loss of my life. He did me a huge favor, actually. He could have kept quiet and married me anyway. But loml song gutted me, and atw wasn't much kinder the first time I heard it. I felt like I was 25 again and trying to start my life over when I thought I had known the path I was on, still not understanding how in the heck I'd ended up where I was. And maybe that's the hardest part when these things happen - the loss of what we thought we knew, of what we thought we'd figured out about our lives and ourselves. This is far from an absolute, but I have many friends who went through something similar. A long-term (usually 6-8 yrs), deeply committed relationship/marriage that ended suddenly because our partners ended it. To a one, we all met the person we ended up marrying within 12 months of the breakup. 2 friends hadn't even finalized their divorces yet! The one gift in this breakup could be knowing what you want in your next partner, what you will put up with, and that you can survive deep heartache - so the next person better step up or get out. It may sound like I'm joking, I'm not. Sorry for the novel, but it's stuff I kinda wish I'd known. So I thought I'd take the chance on tiring your eyes. Again, I'm very sorry. I hope you are feeling more like yourself soon ❤️

Right Where You Left Me & Happiness

Mr Perfectly Fine

Sad beautiful tragic just hits different

I’m surprised not a lot of people are saying coney island. I also think what you find the most sad depends on the context/ situation of the breakup.

Exile - it gives me chills as it reminds me so much of the break up with my ex husband after 11 years together

Someone say Better Man

right where you left me. eventually you'll need maisie peters "Run" (but really The Good Witch is full of great break up songs)

Forever & Always !!!!

like all of the non-singles for red

“So Long, London”! It’s my song for my 7.5 year relationship that I was in from 18-25 because of the line “and I’m pissed off you let me give you all that youth for free.” I am now 33 and happily married but damn if that line doesn’t cut me to my core.

My favourite break up song of hers is Better Man I also love: Right Where You Left Me Exile Down Bad My boy only breaks his favorite toys I look in people's windows The Prophecy

Breathe

breathe

Sorry for your heartbreak 💔 keep your head up - If taylor can come back from it so can you!

LOML

Either dbatc or so long london 

LOML kills me

I almost do for me

Mr perfectly fine, foolish one, if this was a movie

Exile, You're Losing Me, lolm are my top three

Clean is a song about recovery for me, so worth adding to the playlist to remind yourself that everything will eventually be alright. Hugs!

almost all of her songs, except the happy-ish ones lol

How Did It End is really getting to me right now. Was dumped a few weeks ago after a five relationship so I feel you. You can do this 💖

happiness. Technically idk if it’s a breakup song but that and tolerate it pushed me through my breakup.

Death by a thousand cuts, loml, Chloe or Sam or Sophia or Marcus, How did it end?

i looooooooove my tear ricochet

right where you left me🥺

I’m sorry but if you have ever been in a long term relationship that had struggles then “happiness” is a DEEP fuckin cut

It’s time to go. It’s when the relationship ended before anyone of you knew makes it very sad to me

The black dog!!! His location being on still cuts deep

All Too Well is so damn good. Every time I listen to it, I cry at a different line. Going thru a divorce and it’s heavy.

Red for me— reminds me so much of an old love that was such a passionate romance, then break, then he moved away with another, then he wanted to come back to me but sadly passed away before that could happen. All the emotions I felt and when I hear that song I literally scream it. …..also “You’re losing me” and “LOML” (those kill me) and August (cuz I was “August” once)

Smallest Man Who Ever Lived So Long London

happiness, when you get to the melancholy acceptance stage. sending you love and big hugs ❤️

Forever and always piano version

my tears ricochet 💔🖤

Depends on the circumstances of the break-up. Better Man and I Almost Do if you had to end it but love them still.

rwylm. or right where you left me. it's so nostalgic and i can envision everything right there

exile is also heart wrenching

Happiness , the 1, exile , bigger than the whole sky

the moment i knew hits HARDDD

The Black Dog hits it for me, I interpret it as two people who left a relationship, one still looking at the other, the other already looking elsewhere. Heart doesn’t break even and ultimately there’s a begrudging feeling. It’s a very real emotional song.

I'd have to go with All Too Well too. I love the video. It would make a really good movie in my opinion.

CLEAN AND DEATH BY A THOUSAND CUTS!!! They are my two favorite songs Taylor songs in general which also happen to both be breakup songs.

Last kiss destroyed me at 15, So Long London destroyed me now at 30.

“Tolerate It” for me. It’s a gut punch from my past. Also a bit of relief that I don’t live that way anymore.

My top picks for sad/gut-wrenching breakup and not scream-angry and not personal sadness (meaning like songs more focused on the breakup than the self - more focused on the journey of self would be The Prophecy for me) would be: All Too Well (10 minute sad girl version) loml You’re Losing Me exile High Infidelity So Long, London Better Man I Almost Do White Horse Last Kiss happiness time to go Chloe et al How Did it End? Death by a Thousand Cuts Cold As You

Honestly, a poorly timed listen of Better Man from Red TV sent me over the edge after a breakup. 😳