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Listen to it & wallow in despair with us here

1. Arthur Russell – “I Couldn’t Say It To Your Face”
Selected by Daniel Gill of Force Field PR
“Most of Arthur Russell’s songs are about the feeling of a relationship beginning or ending and this is probably the best one he wrote about how hard it is to end one.”

2. Gram Parsons – “$1000 Wedding”
Selected by Royal Trux

3. Annie Lennox – “No More ‘I Love You’s”
Selected by Jimmy Whispers

4. The Cure – “Boys Don’t Cry”
Selected by Pedlar76

5. Tom Diabo – “Suspicious”
Selected by Terry Malts
“Suspicion is always an ear-mark of a rotten and doomed relationship.”

6. Funkadelic – “This Broken Heart”
Selected by Shannon Lay

7. Eldridge Holmes – “Gone Gone Gone”
Selected by Daniel Gill of Force Field PR
“She gone. That about sums it up”

8. gnash & Olivia O’Brien – “i hate u, i love u”
Selected by Flora Cash
“Nice lyrically packed track about the ambiguous aftermath of what might’ve been a decent relationship. And sand in sweaters.”

9. Sarah Vaughan – “Smoke Gets In Your Eyes”
Selected by Tolliver
“Give me three wine coolers, turn this on and watch me cry. It’s fun for the whole family. I love the wordplay – the description of love as a fire, something to be snuffed out. There’s that great tonal shift halfway thru. The singer is ecstatic, humiliated and ultimately broken. Feels bad, man.

10. Camera Obscura – “The Sweetest Thing”
Selected by Alex Rose
“I’m going on a date tonight to try to fall out of love with you”

11. Irma Thomas – “It’s Raining”
Selected by Bunny
“Because nothing lasts forever”

12. Starflyer 59 – “Goodbyes Are Sad”
Selected by Holy Wave

13. The Prids – “Do I Look Like I’m in Love?”
Selected by The Pains of Being Pure at Heart

14. Fountains of Wayne – “I’ll Do The Driving”
Selected by Sophie Gilchrist of Force Field PR
“It might not be an anti-love song per say, but it’s sure as hell not a romantic song.  “I’ll Do The Driving” is a dismissive song about dating a dumb girl with a “certain nothing behind her eyes” and not being sure of where the relationship will go but he’ll just be sure to do the driving.  The best part of the song is the disgust the singer has when they hear “Jumping Jack Flash” and the poor girl messes up practically everything: “She says ‘I love Johnny Cash, the man in red’ I turn my head and pretend not to hear what she says.”

15. Talking Heads – “I’m Not In Love”
Selected by Look Vibrant

16. Prince – “The Ballad of Dorothy Parker”
Selected by Harrison Lipton
“It’s the hottest song ever about *not* hooking up.”

17. Prefab Sprout – “When Love Breaks Down”
Selected by Ablebody
“The most succinct song about breakups ever written: overwrought, sensationalized, idealized to the point of ridiculousness, a perfect summation of the denial we all go through on the other side of love.”

“When love breaks down
The things you do
To stop the truth from hurting you

When love breaks down
The lies we tell,

They only serve to fool ourselves”

18. The Beach Boys – “I’ll Bet He’s Nice”
Selected by Modern Time Machines

19. The 6ths – “Falling Out of Love (With You)”
Selected by Daniel Gill of Force Field PR
“Wow, this song just slays me and pretty much sums up what our annual Anti-V-Day mixes are all about”

20. Eddie Harris – “I Don’t Want Nobody”
Selected by Bonny Doon