Songs I Listened To When Boys Didn’t Like Me Back

A musical taxonomy of the heart

We’ve all experienced the searing twinge, the pummelling blow, the heartbreaking, heart-wrenching devastation that is unrequited love, where hopes, dreams, and fantasies are shattered. It's the apoplectic equivalent to putting all your eggs in one basket, only to have them cracked open and exposed to the harsh reality of love.

In these times of deep emotional peril, I turn to music to bring me through the darkness of unrequited love. Here, then, are the songs I listened to when boys didn’t like me back.

Taylor Swift “You Belong With Me”

This is the keystone pop ballad for the entire spectrum of rejection. You feel for Swift: She’s just a girl in sneakers next to a cheerleader in heels. There’s nothing quite like the feeling of not being good enough, and this song encapsulates that, while still allowing a glimmer of hope to shine through the emotional darkness. The music video also changed my life because Swift plays both girls! It’s a metaphor for her inner struggle. And all of ours.

The 1975 “fallingforyou”

The 1975 are no strangers to unconventional love songs, but this one has to be my favorite. The song takes place on the front end of unrequited love—when your feelings are at their highest and strongest. The song really captures the slow descent into madness that feelings of love bring with them. “According to your heart/ My place is not deliberate,” i.e. you didn’t intend to put me where you did in the back of your heart; “I don’t want to be your friend/ I want to kiss your neck,” i.e., but although you’ve said no to me, I still want more—I still want you! (BRB, sobbing.)

Bonnie Raitt “I Can’t Make You Love Me”

If “You Belong With Me” is our modern unrequited love song, “I Can’t Make You Love Me” is our classic. I don’t even need to add anything here; the song is just exactly right. “You can’t make your heart feel something it won’t”. Bonnie WHY?

Frank Ocean “Bad Religion”

The most sorrowful self-initiated backseat therapy session of all time, “Bad Religion” is truly an emotional journey. Loving someone who doesn’t feel the same way is in many ways a religious experience, you’re practicing one-sided worship. And, as Ocean points out, that’s a really fucking bad religion to follow. Frank chants “I could never make him love me,” and the words pound straight into our chests.

Dolly Parton “Jolene”

This one captures the feeling of your love slipping away into the hands of someone else. Perfect for that special moment when you’re coming in at second best and feeling desperate to maintain your control over a situation, but YOU JUST CAN’T. Dolly Parton, queen of desperately begging for love, sucker punches us right in the feels as she pleads with the other woman for mercy. 

Fiona Apple “I Know”

A tale not of unrequited love, but unrequited ambition. Apple documents the experience of being the other woman, the Jolene, who is there “by the backstage door” to offer escape, but is not the top priority for her man. It’s an aggressive and agonizing song about the emotional whirlwind she’s experiencing knowing that she’s important to him, but not seeing the proof.

Ingrid Michaelson “Maybe”

When you’re ready to take matters into your own hands, when you’ve moved from grief to acceptance, is when “Maybe” comes in. Michaelson advises us to let it go, to be the first one to accept things, and to look toward the future. She croons notes of acceptance, of blossoming in new situations, and leaving the darkness in the past. “Maybe in the future, you’re gonna come back,” but “the only way to really know is to really let it go.” Good advice, Ingrid.