Playlist: 14 Heartbreaking Songs to Make You Cry
Here are 14 heartbreaking songs to cry along with on February 14th (or any other day) for those who need a good emotional release.
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Listening to heartbreaking songs can be cathartic. Romance is not always what it’s cracked up to be, especially for the recently single or those who let “the one” get away at some point in time. If that sounds like you, instead of pretending to be okay like the happiest of couples, give yourself permission to unleash your true feelings.

Here are 14 heartbreaking pop songs to cry along with on February 14th (or any other day) for those who need a good emotional release. Grab the nearest blanket and a pint of full-fat ice cream.

1. Olivia Rodrigo: “drivers license”

You probably saw this one coming, but Olivia Rodrigo’s breakout single (and huge TikTok moment) is masterfully written and produced and is perfect for channeling that first heartbreak feeling from your teens.

2. JP Saxe & Julia Michaels: “If the World Was Ending”

Sometimes even if we’ve accepted a relationship is over for all the right reasons, it would still be nice to know you’d have that person at your side when you need them.

3. Lizzy McAlpine: “I Knew”

Love stories don’t always go as planned; Lizzy McAlpine tells this story in a bittersweet acoustic version of “I Knew,” which paints the picture of someone who thought they knew their ex loved them.

4. Bruno Major: “Places We Won’t Walk”

It’s easy to get hung up on the things you didn’t get to do with your ex, and Bruno Major only needed one phrase to get the point across in this super sad song.

5. Tom Misch: “Movie”

If you lay awake at night thinking about how your ex-partner is doing, what they’re up to, and whether they’ll remember you or not, Tom Misch put it all in a song for you.

6. Amber Ais: “W.C.I.B.M”

It would be a lot easier to get over that person if you could just wake up and hate them. Amber Ais puts that struggle into words in this ballad.

7. PJ Morton & JoJo: “Say So”

He loves me, he loves me not. She loves me, she loves me not. JoJo and PJ Morton try to figure this classic dilemma out in this heartfelt track about what’s starting to feel like unrequited love.

8. Gatlin: “Summer Coat”

Change is inevitable, and so is the end of all kinds of relationships. If you and your person fizzled out and had a short-lived romance, Gatlin’s “Summer Coat” won’t make you feel like the only one with that story.

9. Cyn: “I’ll Still Have Me”

It might feel cleansing to listen to heartbreaking songs all day while balled up in bed, but lets at least make one song about the power of self. Learning to love your own company is a skill that takes work, and Cyn will help with that.

10. Laufey: “Someone New”

Holding to on to someone from the past is just so easy to do, especially when you don’t think you’ll ever be able to replace them.

11. MARO: “You Should’ve Stayed”

If you’ve held back your tears up to this point, MARO’s rich voice and excruciatingly poignant lyrics might just break you down. Feel free to wallow in the abyss of never knowing what you two could have been.

12. GIVĒON: “Heartbreak Anniversary”

For some, Valentine’s Day can feel like their own personal heartbreak anniversary, as Giveon would say. Even a fleeting moment of thinking of your ex years after you grew apart can be painful. Work through it with this record.

13. Gracie Abrams: “Friend”

Basically, if you can’t have all of your partner, why have any part? Gracie Abrams makes a case for not staying friends after a breakup.

14. Lennon Stella: “Goodnight”

A painfully perfect vocal performance with lyrics about never wanting to say goodbye make up Lennon Stella’s surprisingly lighthearted song that you still might end up crying along to.

Bonus… Chloe x Halle: “Don’t Make It Harder On Me”

We can’t leave things on a totally despondent note. For a little recovery after getting through these heartbreaking songs, here’s Chloe x Halle’s anthem about actually knowing you’ve made the right choice about leaving your ex. You got this.

If you were inspired by the melancholic reality of these songs, try making your own songs to cry along with using Arcade by Output, a loop library with easy-to-use melodies and drum patterns; just add vocals. New users get a free trial.

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