The Top 10 Saddest Taylor Swift Songs

10. The Last Time

This song is like when you know you need to stop hooking up with someone who’s toxic for you but for whatever reason you simply cannot. We’ve alllll got that ex. This is the song you put on after you have some good old fashioned ex sex and they hurt your feelings for the 1289436th time just so you can get that good cry out and feel like no for real… this is actually the last time I’m doing that (even though it won’t be). It’s a pity party and I love it.

Notable Lyrics:

“You find yourself at my door,
Just like all those times before,
You wear your best apology,
But I was there to watch you leave”

9. You’re Not Sorry

This is a Fearless era classic. This is the song you play when you actually do end things, but it’s like an angry cry more than a sad cry. The quintessential “I’m done with your shit but it still hurts my feelings” song.

Notable Lyrics:

“All this time I was wasting
Hoping you would come around
I’ve been giving out chances every time
And all you do is let me down”

8. Sad, Beautiful, Tragic

You would think that a song with ‘sad’ in the title would be higher on the sad songs list but what can ya do? This is the relationship that should’ve worked because you loved each other so much but for whatever reason it just didn’t. The way she says “could you just try to listen?!?!?” gets me every single time. Damn, maybe this song is sadder than I think.

Notable Lyrics:

“In dreams, I meet you in warm conversation
We both wake in lonely beds in different cities
And time, is taking its sweet time erasing you
And you’ve got your demons, and darling they all look like me”

7. I Almost Do

Okay, so this might sound similar to a different type of sad relationship mentioned above but it isn’t, okay? This is the relationship that ended (probably for good reason) but you’re not over it, and even though you want to call them again, you never do. It’s another pity party. You’re being strong by not contacting them but you think about them all the freakin time. Damn, that sucks. I’m getting sad just thinking about it.

Notable Lyrics:

“I bet you think I either moved on or hate you
‘Cause each time you reach out there’s no reply.
I bet it never ever occurred to you that I can’t say “Hello” to you
And risk another goodbye.”

6. Forever And Always (PIANO ACOUSTIC VERSION)

Forever And Always is such a jam that you never notice the depressing lyrics. But this extremely rare, god tier version of Forever And Always slows it down and you think, damn… that’s a sad sad song. Nothing sadder than watching a relationship fall apart and it ruins everything you do, everywhere you go, because you’re replaying words they’ve said and thinking what a lie they turned out to be. I’m like tearing up. Okay. Linking the piano acoustic version here.

Notable Lyrics:

“So here’s to everything coming down to nothing
Here’s to silence, that cuts me to the core
Where is this going? Thought I knew for a minute, but I don’t anymore”

5. Back To December

Another classic. I think I forget how good this song is because I’ve known it for so long, but I just read through the lyrics and good god, step on my neck a little harder, Taylor. This song won the Teen Choice Award for ‘Best Breakup Song’ sooo you know it’s good. This is also when she was still pretending to be country so ignore the ‘ain’t nothing’.

Notable Lyrics:

“It turns out freedom ain’t nothing but missing you
Wishing I’d realized what I had when you were mine”

4. Cold As You

Okay, let me be real with you- this is my personal number one. She wrote this song when she was like twelve years old. This song is on Taylor Swift! The first album! And yet it’s inexplicably about dating adult men! Amazing. Dating someone who is unable to communicate, blames you for everything, won’t admit they had feelings for you too… wow, it’s like looking in a mirror. I love this song because it’s versatile. I can cry over literally any guy I’ve ever dated. Love that for me.

Notable Lyrics:

“So I start a fight ’cause I need to feel somethin’
And you do what you want ’cause I’m not what you wanted”

“And you come away with a great little story
Of a mess of a dreamer with the nerve to adore you”

3. Dear John

I don’t know a single chick who doesn’t have a Dear John story. A lot of us even have a Dear John story from when we were 19 so we can literally sing “Don’t you think 19’s too younnnnng” and feel sorry for ourselves. Dear John is everyone’s manipulative ex, it’s the guy who screwed you over so hard it changed the way you think about relationships. Dear John is fuckin DARK. Once you figure out who your ‘Dear John’ is, it’s impossible not to cry to this one.

Notable Lyrics:

“Well maybe it’s me and my blind optimism to blame
Maybe it’s you and your sick need to give love then take it away
And you’ll add my name to your long list of traitors who don’t understand
And I’ll look back and regret how I ignored when they said “run as fast as you can””

“All the girls that you’ve run dry
Have tired, lifeless eyes
‘Cause you burned them out”

2. All Too Well

Is this the best song ever written? Absolutely. It’s Taylor Swift’s best song. BUT it is not her saddest song. Still, you can’t listen to the bridge of this song without feeling some very strong emotions. It’s your Mr. Big ex. I almost don’t need to give this song any context because you already know what we’re working with here.

Notable Lyrics:

“Maybe we got lost in translation, maybe I asked for too much,
But maybe this thing was a masterpiece ’til you tore it all up.
Running scared, I was there, I remember it all too well.
Hey, you call me up again just to break me like a promise.
So casually cruel in the name of being honest.
I’m a crumpled up piece of paper lying here”

(Also just… all of them but I’m not going to copy paste the entire lyrics in here)

1. Last Kiss

Actually just murder me if you ever catch me listening to Last Kiss. I’d rather be dead than feel those feelings. I’m not kidding. This is like, the hard stuff. The rest I can listen to somewhat casually, but I will only listen to if I’m in a very dark place. It just instantly spirals me into the emo zone. It is so, so sad. Be careful with this one… use it wisely. It’s only for when you need a serious cry. It’s like having an emergency xanax script for panic attacks… you should only use it if you think you’ll die without it.

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Notable Lyrics:

“But now I’ll go sit on the floor
Wearing your clothes
All that I know is
I don’t know how to be something you miss”

“So I’ll watch your life in pictures like I used to watch you sleep
And I feel you forget me like I used to feel you breathe
And I’ll keep up with our old friends just to ask them how you are”

“You can plan for a change in weather and time
But I never planned on you changing your mind”

Man, that got dark. Here’s a fun one to get you through the day:

And if you want to hear more of my thoughts on sad Tswift lyrics, you can listen to Schnitt Talk episode 42 here and here.