The Ultimate Female Heartbreak Playlist

Is it a rite of passage, as a music fan, to go through your first heartbreak and immediately dig through all the music you know of to find the greatest heartbreak songs of all time?

How devastatingly beautiful it feels to listen to songs you’ve adored since you were young and finally relate to them. Your brain, overcome with emotion, tries to relate every single lyric back to your specific situation, no matter how much you must twist what’s being sung to make it fit. Maybe your situation was right person wrong time, maybe it was perfect until your partner cheated, maybe it was long and great and fizzled out slowly until it barely even hurt when you finally broke it off, but now some time has passed, and you want it to hurt. Here are my favorite heartbreak songs.

The album cover for Melodrama by Lorde

1.        “Hard Feelings / Loveless” by Lorde

Top-tier production is the baseline for Lorde. With Jack Antonoff producing, every song on the 2017 album Melodrama has no choice to hit exactly where it wants to. Lorde's lyrical skills make the album even more deadly. When the second chorus of "Hard Feelings" ends with the devastating “God, I wish I believed you when you told me this was my home”, a long interlude begins that sounds like a car repeatedly crashing. It goes on longer than you feel like it should (a symbolic choice) and then empties into a quiet but cutting bridge, “Three years, loved you every single day, made me weak, it was real for me”. Then a dance beat plays for the “Loveless” section, in which the singer celebrates recklessness, “Bet you wanna skip my calls now, well, guess what? I like that!”

The album cover for Happier Than Ever by Billie Eilish

2.        “Male Fantasy” by Billie Eilish

This one covers perhaps the most possible bases of any of these songs. Eilish first talks about vices, opening the song with, “Home alone, trying not to eat, distract myself with pornography”. She’s filled with love, desire for hatred (“Just pretending to be alright, convince myself I hate you”), growing pains, and exhaustion (“Can’t get over you no matter what I do”), all sung over a devastating guitar riff. It feels so, so empty.

3.        “Tough Act” by Maisie Peters

There were times when this was the only song that could make me cry. Shimmering piano sets a backdrop. As the song progresses and Peters sings mostly in her upper range, it’s deeply emotional, “Everybody knows that a breakup is better when there’s someone to hate, but you were my favorite way to stay up and I’d say that still”. When the bridge ends, she switches the chorus to a lower octave and cuts most of the music, “I know the reasons, took a little time to believe ‘em/now everything is through, it’s you I wanna call, though.” It all floods back in as she closes the song. The brief barrenness has the effect of taking a deep breath and repeating the reality to yourself as you face the fire.

The album cover for The Tortured Poets Department by Taylor Swift

4.        “I Look In People’s Windows” by Taylor Swift

The first time I heard this song, it made me feel physically sick to my stomach. It reminds me of “Carol of the Bells”, a song I unfortunately hate. Way too ominous. “I Look in People’s Windows” maintains this feeling, but in a more sad than scary way. Swift navigates accepting that she’s an outsider to an ex now, “I look in people’s windows in case you’re at their table, what if your eyes looked up and met mine one more time?” With only guitar and haunting backing vocals, the song is stripped and almost cozy.

5.        “All Too Well (10 Minute Version) (Taylor’s Version) (From the Vault)”

This is my go-to when someone asks me what my favorite Taylor Swift song is. It gives me a ton of nostalgia, but even if you didn’t grow up with the Red album, it will likely have cut quite deep by the time you get to the floaty outro. She reminds herself, as the song fades out, that she didn’t make everything up, “Wind in my hair, I was there, I was there”. Swift creates a tragic image of an autumn love story with enough stunning lyrics baked in that even if you’re not recovering from a three-month long fall fling yourself, you’ll find your place in the track. She has the anger (“I was thinking on the drive down, any time now, he’s gonna say it’s love, you never called it what it was”), the depression (“Time won’t fly, it’s like I’m paralyzed by it/I’d like to be my old self again but I’m still trying to find it”), the affirmation that it was all real, and the reminiscing (“You taught me ‘bout your past thinking your future was me”). What a song.

The album cover for Older (and Wiser) by Lizzy McAlpine

6.        “Soccer Practice” by Lizzy McAlpine

McAlpine opens the song fingerpicking in open D guitar tuning. The song picks up but never quite climaxes. Instead, it turns dreamy as the second chorus ends and begins to play, muffled, in reverse, almost sounding like actual words as it fades out. She discusses denial, the future, persistence, fear, and exhaustion, summed up best with, “We could’ve had it, but then again, we never could’ve done it, I was weaker then.”

The album cover for eternal sunshine by Ariana Grande

7.        “I Wish I Hated You” by Ariana Grande

With only a simple keyboard riff playing behind Grande’s voice, this song feels like sitting in an echoey waiting room, “Just two different endings: you learn to repair, and I learn to keep me in one place”. It’s one of Grande’s best songs, lyrically speaking, and also one of the best on her 2024 album eternal sunshine.

8.        “I Should Hate You” by Gracie Abrams

Like Grande’s similarly titled song, this track is mostly stripped. Acoustic guitar plays throughout, and the song builds in the bridge, but comes back down quickly. It feels as if the song itself is on its deathbed, “I feel stupid, like I almost crashed my car driving home to talk about you at my table in the dark”. I had a hard time listening to it in the months following its release because of how treacherous the combined sound and lyrics felt.

The album cover for emails i can't send fwd: by Sabrina Carpenter

9.        “Thing I Wish You Said” by Sabrina Carpenter

Stripped and feverish, this song almost feels like Carpenter is whispering to an ex, trying to find a gap to bridge in the space-time continuum, “I’m watching everything that you do, I can’t get your songs out of my head or your hair out of my room”. The song is perfect for almost every situation because it’s so hypothetical. It’s literally things she wishes happened but didn’t, such as an admittance that “everything reminds me of you, nobody gets my jokes, everyone here thinks I’m fucking rude”.

The album cover for Florescence by Maisie Peters

10.       "If You Let Me (featuring Marcus Mumford)” by Maisie Peters

This song feels like a hug on a long sad night, reminding you that everything will be okay. It opens with Peters' falsetto, which blends pleasantly in the second verse with Mumford’s low notes. This song may hit the most accurately when you’re lying in bed crying, but I would recommend playing it while in a quiet place in nature as the sun rises or sets. Going from “Look at me, baby, while you put me down/now I’m not, now I’m not your friend/but I’ll be alright if you let me” to “Tears dry, lights off/fall asleep baby so the hurt stops and I’m beautiful, beautiful alone” is cathartic.

Listen to all of these songs in one place here.