Lesser-Known Taylor Swift Songs to Get You Through Every Type of Breakup

A fair amount of people don’t know this about me…but I am a huge Taylor Swift fan. Huge.

I remember everything about the moment I heard my first Taylor Swift song. I was riding in the passenger seat on Woods End with my Dad in his Prius, and Teardrops on my Guitar came on the Sirius XM Country station and I was like hold up - this is fucking beautiful.

I didn’t say the “f word” at the time, because I wasn’t allowed to (and my mom still doesn’t like it), but in my head I was like…fuuuccckkk yeah.

I heard You Belong With Me next. Couldn’t take it off repeat. I watched the Love Story music video on our family computer and remember dragging my mom over to watch it with me.

Isn’t this amazing?” I had said, my jaw dropping with each new scene.

“It’s really nice!” she told me, and then went back to cleaning the kitchen.

My mom didn’t get it. This was magic. I was hooked.

Because I became such a fan at an early age, I’ve listened to every Taylor Swift song in existence and that includes scouring the internet for her unreleased demo songs.

Taylor Swift is undeniably a fantastic lyricist. I wasn’t crazy about her edgy-snake era, sometimes I find a few things she does awkward - but I love her unconditionally, first and foremost for her lyrics. They’re raw, authentic, vulnerable, and that’s what FluentlyForward is all about.

So let me provide you with some songs of hers (not the ones on the radio that you know of) to help you with your breakup - any breakup at all - because she covers the full spectrum of emotions wonderfully.

If you were with a toxic piece of shit who loved to make you feel bad…

Listen to “Cold as You”. This is from her very first album - I think she was 15 or 16 when it came out - and when you listen to this song you’re like woah, Taylor, no one should be hurt that bad before age 18.

The line, “so I start a fight, cause I need to feel something. And you do what you want, cause I’m not what you wanted” will crush me every time. Take solace in the fact that Taylor went through this at a damn young age, and came out the other side better off for it!

If you were totally blindsided by your relationship, it went from 100 to 0 real quick…

Listen to “Forever and Always” aka, yes, the Joe Jonas song. This song is a goddamn masterpiece, I don’t know how it never made it to radio.

It hurts so deeply when someone drops you quickly, mainly because your heart is broken but there’s also a deep wound to your pride. It’s surprising to have someone change their feelings on you, and it almost feels like a double betrayal. Taylor captures it perfectly in this song. Sadness…but also rage.

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If you broke up with your partner and you unfortunately still have to see and interact with them every day…

Check out “Story of Us”. It’s rumored that Taylor wrote this song about John Mayer, when they broke up, and ran into each other at an award’s show a few weeks after. Apparently people noticed that Taylor was doing everything she could to avoid the musician, and we’ve all been there - but for us it’s normally a situation like a college party, work, or the lunch room. So a bit less glamorous, but similar nonetheless.

If you’re just terribly sad over losing who you thought was the love of your life…

Get ready to bawl with “Last Kiss”. This is also about Joe Jonas and really in writing this blog post I’m realizing that Joe did a number on our girl. There are some lyrics in this song that do in fact make me cry every single time, like “I’ll watch your life in pictures, like I used to watch you sleep. And I’ll feel you forget me, like I used to feel you breathe.”

Honestly I’m almost getting misty just thinking about it. Listen to “Last Kiss” and just let the tears out.

If you know that your ex wasn’t good for you…but you can’t help but miss the shit out of them…

“I Almost Do” from the Red album. God, what a masterpiece. Taylor sings about how she’s cut this man out of her life, and he might think that she hates him, but the opposite is true. She wants to reach out, she wants to get back together, and she almost reaches out…but it always ends as an ‘almost’.

Reserve this song for the person who did the biggest number on you…

“All Too Well”. All. Too. Fucking. Well. This song is a bit more well known since Taylor performed it at the Grammy’s, but I don’t believe it ever made it to radio. This song is about Jake Gyllenhaal and Joe Jonas can take a fucking seat because I don’t think anyone messed with Taylor the way Jake did.

Apparently the original version of this song was 20 minutes long. It’s shorter now (5:29) but is still able to tell a complete story about Taylor falling in love, learning about someone, revealing herself, and then painfully having the relationship end. It’s heartbreaking. The line, “you call me up again, just to break me like a promise. So casually cruel in the name of being honest” is rumored to be about when Jake called her, and admitted to cheating. I cry literally every time I hear it.

When you know your relationship is over, before they even do…

Listen to “The Moment I Knew” (Red album deluxe track). Remember when I mentioned Jake? Well he’s back, but this time he’s standing up Taylor at her goddamn birthday party and she’s excited for him, wearing a pretty dress, and he never comes and it’s super embarrassing and she knows then…wow this guy gives 2 shits about me, I’m aware this relationship is over by his shitty actions alone.

Fuck you, Jake Gyllenhaal!

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If you’re in a bad relationship (with yourself)…

Check out “Tied Together with a Smile”. I believe Taylor wrote this about a girl who was suffering from an eating disorder in her high school (it’s from her debut album). It’s a really sweet and insightful piece about what it’s like to be hanging on by a thread, but putting on a good show so no one notices.

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If your ex tries to get back with you (after they literally were the one to break up with you)…

Sing along to “All You Had To Do Was Stay”. It’s great. I love this song. The theme is basically: Fuck Yourself. Reserve this one for the fuckboys who only want you when they can’t have you.

When you want to be petty about your ex in an old-school country way…

Check out Taylor’s unreleased songs “I Heart Question Mark” and “Permanent Marker”. (You can find these on YouTube or Soundcloud most likely). I think she wrote them in high school, but they’re fun and angry tunes to jam out to.


There you have it! A number of other great breakup tunes of hers that don’t fall into these specific categories are:

  • Clean

  • Red

  • I Knew You Were Trouble

  • The Last Time

  • Sad Beautiful Tragic

  • Dear John

  • Haunted

  • If This Was A Movie

  • Tell Me Why

  • You’re Not Sorry

  • Should’ve Said No

And literally so much more, but I don’t want to re-list super popular ones. To anyone going through a breakup, my heart goes out to you! And if you want any tips on how to heal your breakup, check out my post on that here.

Swiftily yours,
S