Every Song on My Breakup Playlist and Why It's Perfect

Believe it or not, I have been fumbled. More than once, in fact! In 2017 it was because I wanted to move away and he didn’t. In 2022, it was because he wanted to move away and I didn’t. Most recently, it was because the prospect of drinking a cocktail across the table from my sister after having raw sex with me for 18 months ostensibly felt like far too much commitment.

Luckily, I happen to have curated the perfect remedy for situations like these. Imagine me as your grandma, rushing to your side as you lie on the couch, peddling a superstitious traditional remedy for your ailments — except instead of a lukewarm concoction of probably expired miscellaneous liquids from her kitchen it’s a Spotify link, and instead of a nasty cold it’s the fact that Todd won’t text you back anymore.

My breakup playlist is the perfect length for a spite-fuelled workout or a productive cry (one hour). It is arranged according to the five stages of grief (obviously). I believe it is categorically without flaw, and I’m going to break it down for you, song by song, until you believe so too.

A note before we dive in: This is my real breakup playlist. That means it’s full of songs I really listen to. I’m aware my taste isn’t particularly niche or groundbreaking, and it’s important to me that you know I’m not trying to do an Apple Music 100 Best Albums sort of thing. I like pop music and I listen to a lot of the same artists. This playlist has a lot of pop music by a lot of the same artists. This is Every Song on MY Breakup Playlist and Why It’s Perfect. Your breakup playlist might look different, and that’s OK! You still deserve to be broken up with just the same <3

Denial

Whenever He Asks — Gatlin

Sometimes a breakup is like trying to turn on the shower at someone else's house in that you have to try it a couple times before it really works. This song is about fucking your ex and it's in 12/8 time! What more could a girl ask for?

4Runner — Alix Page

At first it might be hard to tell why I think this is a Denial song. On the surface, it's a pretty standard song about the aftermath of a formative relationship. Singer misses lover. They shall be the benchmark for every relationship Singer enters henceforth. No one's denying that!

In fact, why I put this here has everything to do with the bridge. She just repeats "I can take it back anytime I want to." Over and over. It's kind of haunting. To me, it sounds like she's trying to convince herself it's true. "I can take it back"; "I can become myself again"; or, rather, "I can become the person I was before you again."

The "it" in "I can take it back" is innocence, naivety. (Didn't Taylor Swift write something about giving your youth away for free?) But Alix can't take it back, and neither can you. No matter how many times you repeat it in a song, you can never be unscathed by the person you dated when you were 19.

Better Man — Ber

Envisioning a hypothetical run-in where you get to finally tell off your ex, just like you should have a thousand times while you were dating but were too chicken, could be thought of as a way to trick yourself into believing they're still in your life. Textbook denial!

This song also has glimmers of the next stage of grief, and I appreciate foreshadowing. "If you get the chance to look me in the face and say you want me back...please don't (loser)."

GLAD IT'S OVER — Imani Graham

If Better Man has glimmers of Anger, GLAD IT'S OVER has beams of it. Quite frankly, it's only in this category because Anger was getting full and because it says "You can tell everyone you know that you're glad it's over, but you're lying" and "So drunk, wasted, off jack or tequila." Plus, because of the spacey production and Imani's plain-spoken (plain-sung?) delivery, it also reads to me like she's trying to convince herself she's really GLAD IT'S OVER.

Extra points for that piercing piano ostinato throughout.

Anger

All My Friends — The Wldlfe

I do not condone the lyric "Should've known it was a game you were starting, Mario Kart-ing." I do condone that little lick the lead guitar (I think?) does between phrases of the chorus.

This is for that fun stage of a breakup where the girlies (vibe, not gender) remind you of every single shitty thing your ex did until you're a little too drunk and just pissed off enough to finally book that balayage you've been thinking about.

You're Just A Boy (And I'm Kinda The Man) — Maisie Peters

Put me on Maisie Peters' marketing team and the next album is 100% funky pop-rock laying into a boy who ain't SHIT! (Seriously, this is her specialty. I can name five without even opening Spotify. Boy, Not Another Rockstar, Blonde, Lost The Breakup, Psycho. You don't know I didn't open Spotify. Honour system?)

You're Just A Boy is what happens to you immediately after the All My Friends hangover wears off. All of a sudden, the time you used to spend making dinner with your ex feels less like a gaping void and more like an open door. You're waking up early to go to the gym; you remember you have hobbies and interests and you start getting really good at them. And your ex will never get to reap what you're sowing because they couldn't fuckin' act right. Nothing inspires like spite. Hey that rhymed!

So Sick Of Dreaming — Maggie Rogers

I love when anger is blatant and crude as much as the next girl but, god, isn't there something special about understated fury?

So Sick Of Dreaming is exasperation and exhaustion. It is sitting across the table from yet another finance boy/crystal girl/barista they who likes you a lot but wants to be super real with you and let you know they're not ready for anything serious but are down to keep going on fun dates if that's cool with you haha? It is the white-knuckled grip your brain has on the conviction that what you want in a partner isn't too much to ask; that you deserve it. Even — and especially — when your newfound celibacy makes it harder to believe.

I am also a sucker for a spoken-word bridge.

Pushing 30 — The Sunshine State

It's a tale as old as time: You start dating older men because you believe they'll be more mature and are promptly electrocuted by the stark reality that the 30-year-olds who date 23-year-olds only do that because people their age have standards they can't meet. Remembering how pathetic life will surely be for a man with grey hairs who still goes to college parties won't undo the damage, but it's a start.

Bargaining

25 — Alix Page

When I finally put together a version of my time machine that works, the first thing I'm doing is listening to this song for the first time again. I was waiting for the bus Montreal's unforgiving January on my way to a party with a rebound I didn't really care about, and I was about to turn 25. It provoked a reaction like when a movie mentions the city you live in. ("Hey that's me!")

The second verse is what's Bargaining about this song, for me, and it's also the part where I started believing in god again — because nothing mortal could sound like that. (If you use horns and strings in a pop song I'm proposing.) "So I got a tattoo, burned up on the freeway, my mom told me I seem happier these days." The things we do to convince ourselves we're over it!

I'll also mention something else I admire about Alix Page here. It's kind of unrelated to breakups but I don't know where else to put it and if I don't share it somewhere, with someone, black bile will start leaking out of my pores or something. On a couple songs (4Runner included), instead of expressing intense grief with wailing vocals, she turns up the production. At the emotional apex of 25, she's not belting — her voice is almost a quaver — but the drums are pounding, the horns are blasting, and the guitar is sustaining a screeching trill that would be hard to listen to on its own.

You can barely find her voice amid the instrumental chaos, and that's exactly how it feels when you have to go to work the day after hand-delivering a cardboard box of sweaters that once made you feel safe to a stranger whose future children you once named.

Never Going Home — Maggie Rogers

Cut the sappy shit, it’s time to have fun! Welcome to your post-breakup slut stage. It’s a rite of passage; a time-honoured ritual. Put on your red lipstick like a hero, babe, it’s time to make out with a stranger in a dive bar bathroom! 

If I’m ever in a coma, put in my AirPods and play the bass solo before the bridge. I promise you I’ll wake up and start dancing.

Therapy — Maisie Peters

The deepest embarrassment you will feel during a breakup is not deleting photos, cancelling future plans, or returning borrowed items. It's calling your therapist to tell them you:

1. Did not take their advice.

2. Would like to start coming in weekly for the next little while, please.

This song is that sensation and it will possess you to bust a move in the grocery store.

Easier — Nia Hendricks

I am not happy Nia Hendricks went through whatever she went through to make this song, because oof, but I am grateful because at least now we have it. Horns in pop songs are back!

There comes a moment in most breakups where you have to almost physically restrain yourself from reaching out to them. Not because you miss them, necessarily, but because you're used to hearing every mundane update from their life — and not knowing how their passion project is going or if their dog finally stopped rifling through the bathroom garbage is making your eye twitch.

Easier sounds like the deep breaths you take to stop yourself from calling them. A silly little ritual you force yourself through to stay sane. (Bargaining!)

Depression

Paint My Bedroom Black — Holly Humberstone

My sincerest apologies to everyone within earshot when Holly Humberstone's debut album is mentioned; I did not act Normal about it when it came out and I cannot act Normal about it now.

Paint My Bedroom Black is for when your self-care routines stop working, the thrill of hooking up with new people wanes, and your rediscovered hobbies and interests no longer distract you from what you're really feeling: fucking sad. It's a song for hibernating in your room with your creature comforts. And it's the frontrunner for the Best Opening Song category in the 2024 GMAs (Gabby Music Awards).

King of Disappointment — Jem Cessar-Daley

The title kinda says it all with this one. It's a song for feeling sorry for yourself while reminiscing all the times your ex let you down. Not a fun feeling, but Jem's dreamy vocals and the rolling beat make me chase it.

There's also something ironic and, I think, funny and biting about calling someone the "king of disappointment." Like, yeah, you're the uncontested champion...of falling short and breaking promises!

Listen to the triple j version too.

Automatic — Alix Page

It is a grave mistake to direct all your disdain outward during a breakup. Self-loathers, make some noise!

Automatic is kind of like the inverse of an Insecure Yearning song (which I conveniently wrote about earlier this year!). Call it Insecure Grieving, maybe. "I'm hard-wired to be a piece of shit; I fuck up every relationship I get into; I can't stop myself from treating people like garbage; this always happens; it's automatic."

It's normal to feel this way, but I would advise one not to stay in it for too long. No one is hard-wired to be a piece of shit. You can do better next time. In fact, you must.

Maggie Told Me You Got A New Girl — Caroline Culver

Don't shoot the messenger, but someday you will learn your ex has a new partner. And, at dinner, you will say "That's good! I'm happy for them 🙂" All the while, something primal and unhealed will have awoken within you, and you'll spend the next three days stalking the new partner on Instagram and listening to Maggie Told Me You Got A New Girl. At least the latter will make you feel better.

Acceptance

There It Goes — Maisie Peters

A close friend once told me there's two levels of "over it" in a breakup. There's "over it" where you know it was for the best and you no longer miss being with them, and there's "over it" where you stop thinking about it. The second "over it" comes later, and you usually don't realize you've reached that stage until, one day, you think about your ex again and realize it's been months since you thought about them. That, in itself, feels like a win: This used to consume you, and now it doesn't. You thought you'd never move on, and you already have.

There It Goes sounds like the joy you revel in after reaching the second "over it." It's a sacred internal celebration — even if you tell your friends, "Hey! Remember [ex]? Well, I'm really over them now," no one can understand how deeply the heartbreak cut you and how liberating it feels to know you've reached the other side except you. Plus, going out of your way to tell your friends you're "really over someone now" sounds like a lie.

Finally, thank you Maisie Peters for being brave enough to defy the chorus-only TikTok song music industry gods and write a bridge like this.

Room Service — Holly Humberstone

An earlier iteration of this post was titled "Every Song on Holly Humberstone's Paint My Bedroom Black and Why It's The Perfect Breakup Album." Obviously, I decided against that, and perhaps someday I will recount the gripping narrative of desolation, codependence, and eventual inward homecoming it evokes, but for now I have settled on highlighting the first and last songs.

To me, Room Service is about that eventual inward homecoming — the return-to-self you experience in the wake of heartbreak. It's the safety you feel when you become aware that you can be happy without a specific person, that you can do all your favourite things — even the ones you've become accustomed to doing with your ex — by yourself. And it won't be the same, but it will be good. (I'm reminded of that tweet that was like "Situationships aren't all bad; you often learn about a new brand or restaurant.")

"I'll fill the calendar with plans for you, my dear," Holly sings. "We'll get room service." She addresses herself in the second person because, I think, it's easier to reassure yourself from outside yourself. She promises to build a good life for the part of herself that will always be hurting as the part of herself that is healed, and this song will make you feel like you can do the same.

When You Know Someone — Valley

It's 2024 and Valley is making smash-your-fist-through-your-parents'-drywall pop-rock again. And there's a harmonica in it! Nature is healing!

When You Know Someone is about losing a loved one to their own misery and the relief you feel when you realize you no longer have to carry it with you. Of course, you should be there for the people you care about when they're going through a hard time, but I think it's important to distance yourself when being in someone's life has begun to have negative consequences for your own. Boundaries etc.

The title of this song is a fun "gotcha," too. The chorus ends with "When you know someone, you really know someone, someone like me" — as if to say "sorry you're too emotionally constipated to let anyone get to know you beyond a superficial level. Me on the other hand? I'm nurturing meaningful community with people I truly admire despite the discomfort the prerequisite vulnerability causes! Avoidant attachment is a disease, get well soon XOXO."

Also, the outro. The band said it's "the things you remember about someone." For science, I ran through the words while thinking about each of the three most recent people I dated, and I had specific memories about every lyric with each one of them. I dare you to try it.

Massachusetts — Jensen McRae

We are years removed from the initial blow at this point. We are reminiscing fondly — we are mended enough to be able to reminisce fondly — about the highlights of a relationship that once was.

Massachusetts (guess how many times I had to check I spelled it right) is a love letter to the experience of having known someone deeply. Appreciation for the parts of yourself they influenced. "When someone asks me who's my favourite Batman, I'll think of you and say 'Christian Bale,'" "It's getting darker so I turn you down but I can't turn you off."

Everyone is a puzzle made up of pieces they took from people they've loved; everyone is a canvas splattered with splotches of colours no longer in their palette. This is the ultimate Acceptance song because it's secure enough to say, "Thank you, despite everything, for changing me."

If you read this whole thing, just know I love you romantically. As a reward, you can listen to my full breakup playlist below. Every song on it is perfect, and now you know why.