Super sad love songs.

Question

Bonnie · Answer

Better be home soon - Crowded House: So angsty, so deep

Eric · Answer

Sarah McLaughlin’s - “Ice Cream”: Brings tears… every time

Alyssa · Answer

Try and love again - The Eagles: Need I explain more. This one always gets the tears going.

Lisa Guo · Answer

ed maverick acurrucar: some high school simple chords with a sad Mexican voice.

JDJ · Answer

Walk Away (Ben Harper)

Nic Hade · Answer

Romeo and Juliet: It’s just that the time was wrong.

J Gutz · Answer

Looks Like Rain: “But I'II still sing you love songs

Written in the letters of your name

And brave the storm to come

Oh, it surely looks like rain ”

This song turned 50 year old last month but it still hits.

J Gutz · Answer

Dan Fogelberg’s Same Old Lang Syne: Drinking toast to time with this Xmas themed love song

Nadine Bautista · Answer

Lucy Rose - Shiver: A song about regrets…

lauren o · Answer

Joey (Concrete Blonde) : I think sometimes about how Johnette Napolitano had the melody for "Joey" but put off writing the lyrics until the rest of the album was done and she was in a cab and had no more time. "I knew what I wanted to say, but I wasn't looking forward to saying it."

Amanda · Answer

Amber Run - I Found: Sometimes I have to change the song before it ends. Depends on the day 😬

Meredith · Answer

the world spins madly on: By The Weepies. Enough said.

Unicorns · Answer

most of the time, bob dylan: Best sung while driving and looking off into distance. Betty lavette has a great version too.

Steve M · Answer

less (Olivia Rodrigo): 😢 If it wasn't for my antidepressants I'd be crying myself to sleep every night to this song.

Amy · Answer

The Luckiest (Ben Folds): 🥺

Soleil · Answer

Don't Know How To Keep Loving You - Julia Jacklin: what’s worse than falling out of love and into boredom? 💔

Spines, Flicks, and Wax · Answer

Miss You by Harold Melvin and the Blue Notes: I always feel the anguish in this one.

Nicole Anderson · Answer

I’ll be seeing you: This song breaks my heart every time I listen to it. Billie’s voice aches and the lyrics speak to the tangled mess of love and loss, and how they haunt you in the present — but also the beauty in that.

seán patrick john paul george ringo doran · Answer

Betray /// Son Lux: You will betray me, baby, and I will be true

I only ask, may I share Dinner with you?

MRP · Answer

Blue Bayou: This song makes me homesick for somewhere.

pairofgeese · Answer

i just don’t think i’ll ever get over you by colin hay

Hallie · Answer

Absence by DYAN: The wavelike synth. The soulful vocals. The outro sax. Feelings! Feelings! Feelings!

Dylan · Answer

crowd sourced crying (a playlist): BREAKING NEWS: crying is IN for 2026! when in doubt, cry it out!

⭒ crowd sourced from all your responses to my sad song request! being vulnerable is cool. thank you all for sharing ♡

⭒ let me know if i've forgotten any ♡ i will continue adding your songs to it as more recs come through :)

⭒ PS sorry i only have evil spotify but if anyone wants to make a playlist on other platforms please go for it! hugs ♡

~

cc: @Spines, Flicks, and Wax @S.P.A. QUEEN @Jess s @Rish @AMB @Samantha Culp @Meaghan @Leanh @Mary Kathryn Paynter @Evangeline @Going Analog @sam @jozef @Ginny Branch @Minna Kelly @Noah Morse @Daniel Menegaz @Lanh @Michael Bolognino @Steven Weill @Miranda @Guido @Lida Richardson @CITIZENACTUAL @Geren @Hannah @Neal Lindsay

Edit: wow i'm so overjoyed by how many of you responded to this request. heart is full. what a gorgeous collection of crying songs!!! i'll do my best to keep adding the new recs as they come through :) xx

Sarah Cooney · Answer

Houses: I think of this as the counterpoint to "Suite: Judy Blue Eyes"--Judy Collins wrote this after dreaming about Stephen Stills one night. I'm obsessed with their fifty-plus-year-long connection.

claudia · Answer

The Gold (Phoebe Bridgers Version): this version specifically

Gail · Answer

There’s a possibility: It’s 2009 and your vampire boyfriend just dumped you deep in the Washington woods. Here’s a perfect song to listen to as you disassociate in front of a three panel window for three months.

Amy · Answer

The Blower's Daughter (Damien Rice): This song makes me feel so sad.

Amy · Answer

Night Shift (Lucy Dacus): A lost love song to play at full volume