Happy Valentine’s Day! I’m in pain. Are you also in pain? Would you like to be? Well, have I got a playlist for you.

As long as I can remember, I’ve loved sad songs. To the point that I have been banned from making party playlists by more than one friend group in my life.

In fairness, it’s not necessarily that I like them because they’re sad, I like happy songs too—there are just so many great sad songs. I simply love good music. And I’ve always been willing to let it tear me in half to get to the best stuff.

Plus, there are few brands of sad songs more cutting than sad love songs. So, if Valentine’s Day is meant to be a celebration of love, why not take a musical look at how powerful love is…by listening to songs about how completely it can break you!

Without further ado, 10 of my all-time favorite heart-wrenching love songs to listen to this Valentine’s Day:

“I Love You, But I’m Lost” – Sharon Van Etten

What more explanation do you need? The title says it all. I especially recommend the live solo performance above.

To be fair, I could really have put any pre-Remind Me Tomorrow Sharon Van Etten song on this list. Her whole discography crushes me. It’s great. Other treacherous titles from this album include “Your Love Is Killing Me,” “Break Me,” and “Nothing Will Change.” Listen at your own risk.

Sharon also dropped a new song “Porta” last week and will be on a massive tour this summer with Angel Olsen and Julien Baker, you won’t want to miss it.

Lyric that especially fucks me up: “To know somebody in and out, after a while it’s a real challenge”

“Natural Light” – Tomberlin

This song guts me. It’s really simple, just a quiet repeating acoustic guitar line and straightforward lyrics about remembering someone you used to be close to. But it HURTS. Every little nostalgic phrase hits me right in the heart. I think it’s because it’s so simple. It doesn’t sugarcoat anything. It’s harshly and beautifully real.

Tomberlin also dropped a new song “idkwntht” in January and should have their second album coming later this year, so keep an eye out for that.

Every lyric in this song hurts me, but the fatal blows of the chorus are: “I found a picture from before the fight – we’re in natural light, and you’re sitting on my lap like everything’s alright.”

“I Can Change” – LCD Soundsystem

This one is sneaky. It’s upbeat and has some excellent vibe-y synths throughout. It’s got so much classic LCD charm in the rhythmic repetition of “I can change” that it’s easy to forget how truly vicious it is when that lyric changes from the first to second chorus.

It starts as “Never change, that’s just who I fell in love with,” assuring their would-be partner they love them as they are. Then, it switches to “I can change, if it helps you fall in love.” They’re so desperate to be with this person that they’ll forgo the acceptance and unconditional love they just offered.

Ezra Furman also has a great acoustic cover of this track, which was featured heavily in season 2 of the Netflix series Sex Education.

Additionally rough lyrics: “There’s love in your eyes, but maybe that’s just your love of fights.”

“Riches and Wonders” – The Mountain Goats

The Mountain Goats are notorious for their delightfully sad music, often dealing with family trauma, abuse, and occasionally the darkly comic pain of divorce – like in their recently TikTok-viral classic “No Children.” But every once in a while they release a quietly overwhelming ballad about young love. This one’s my favorite.

Lyrics that should be banned for being too sad: “I keep you safe from harm, you hold me in your arms, and I want to go home. But I am home.”

“I Need My Girl” – The National

This is another Sharon Van Etten situation where I could really just include the entire album.

That said, what gets me about this song is how precisely it nails down two key experiences:

  1. How when you really miss someone, the things you linger on aren’t just the happy times. You remember the crazy, difficult moments too, and you even miss those.
  2. When you miss someone, it doesn’t matter how well you’re doing in every other part of your life. Nothing feels good because they aren’t there.

Cruel & unfair lyrics: “I am good, and I am grounded. Davy says that I look taller. I can’t get my head around it, I keep feeling smaller and smaller. I need my girl.”

“Exile” – Taylor Swift Feat. Bon Iver

I’ve never been a big swiftie (no hate, just not my jam) – but take her saddest pseudo-indie-est record (produced by Aaron Dessner from The National) and add some extra Bon Iver sauce on top? You got me, I’m in.

The overlapping vocals capture the fall of the relationship pretty perfectly. The harmonies collide with the emotionally dissonant, competing lyrics – “you never gave a warning sign” vs. “I gave so many signs.” But perhaps the biggest gut-punch comes from the title itself, “Exile.” The transition from feeling at home – not in a specific place, but simply in the presence of your partner—to feeling removed from your own life and without any direction or refuge.

The titular lyric: “You were my town, now I’m in exile seeing you out.”

“HYD” – Hayley Williams

Hayley Williams may be most known for her late 2000s pop-punk bangers, but her 2021 record – her sophomore solo album, FLOWERS for VASES / descansos – has some moody ballads that can rival the best of them.

The record, which was written & recorded entirely in isolation during the pandemic (seriously, she plays every instrument on the record) is a major achievement that dives into some of the much more subtle gray areas of her divorce. It acts as a perfect companion to her indie-pop solo debut, Petals for Armor, released only a few months before, which focuses more on dancing out the anger.

This track specifically floats back and forth narratively between scenes reminiscent of her own marriage, and others seemingly echoing her mother’s. It digs into how, even in darker relationships that are better off abandoned, there is some faint memory of love that fuels an almost nostalgic curiosity – to wonder how they’re doing since you left them, and how they view you now.

I need anesthesia before I hear this lyric: “In a million years, never thought I’d see the day you would choose your fear over me.”

“Moon Song” – Phoebe Bridgers

This one dives right into its searing depiction of an unrequited—or at least, deeply skewed—love, brutally describing the end of a long night out with their would-be partner. She lays bare how a harmless drunken makeout could mean so much to her, all while knowing that her partner would have shared that moment with anyone. She sings, “You couldn’t have stuck your tongue down the throat of somebody who loves you more.”

If violins make you teary, you should also check out this live performance she did with instrumentalist Rob Moose for Jimmy Kimmel Live. Phoebe released an EP with Rob Moose, titled Copycat Killer, which has orchestral reimaginings of four other tracks from her 2020 record Punisher.

Phoebe’s just mean for this one: “So I will wait for the next time you want me, like a dog with a bird at your door.”

“Ketchum, ID” – boygenius

I could listen to this trio harmonize the phonebook, and it would break my heart. But they still decided to write perhaps the most wistful and yearning song ever, just to send me over the edge. I take it very personally.

Also, I tried not to repeat any artists on this list, and while this supergroup that is ⅓ Phoebe Bridgers may seem like a copout in that regard, I stand by it. The verses of this track sung by Julien Baker and Lucy Dacus are the bits that really cut me. Listen to Lucy sing “Everyone’s around, and I hear you smiling, you say ‘I love you’, I say ‘You too’” and try not to cry. I dare you. She hears her partner smiling? Are you kidding me? I’m done.

Ow ow ow ow ow: “Being in love is the same thing as being alone, given the sorrows and company. Nothing to say, stay on the phone. I’m sorry I do not know what else you want from me.”

“A Case of You” – James Blake

WAIT. Wait. Ok. I know it is sacrilegious to be including a cover of this iconic song. So before I even say anything else, here’s a link to the original Joni Mitchell version. Don’t fight me.

With that out of the way, I have one shameful confession: I heard the James Blake version first, and I kind of like it better. Not sure why, I usually am more of an acoustic guitar person than a piano person, and I usually gravitate more towards traditionally feminine voices… but something about James’ shaky yet clean vocal riffs and the brief silences between the chords he strikes on the piano really get me. It’s at least worth a listen if you’re a fan of the original.

Famously sad line: “Go to him, stay with him if you can, but be prepared to bleed”

Bonus recommendations & their cruelest lyrics:

First Love / Late Spring – Mitski – “One word from you and I would jump off of this ledge I’m on, baby. Tell me ‘Don’t,’ so I can crawl back in.”

My Heart Got Caught on Your Sleeve – Lucius – “I am lost in my own home.”

Love – John Lennon – “Love is asking to be loved.”

Love More – Bon Iver (Sharon Van Etten cover) – “I was younger then, I had nothing to spend but time on you, but it made me love more.”

Rollercoasters (Live on NPR Tiny Desk) – Tank and the Bangas – “I couldn’t wait to tell my friends what it felt like from the very top, and that’s when I knew rollercoasters were for people like me, who have never been in love.”