Songs that you just cannot listen to after a break up. Number one for me is What Becomes of the Brokenhearted. Man, that’s hard to listen to when you’re hurting.
Al Green’s version of How Can You Mend a Broken Heart is also pretty damn unlistenable when in the throes of GODDAMIT, WHY???
And you know what else? I can’t stand the rain, either. I’m partial (or should that be saddened by) to Ann Peeble’s version.
Wow, I guess I get really R&B when my heart is broken.
Fuel’s ‘Bad Day’ http://www.youtube.com/watch?v=TPVhxvPlOZQ gets me every time; think it must have really hit the mark when it came out, in whatever relationship I was in at the time. (For what it’s worth, I’m really closed up about negative emotions, and can relate to the gal in the song, and feel bad for the guy singing…while feeling bad for the gal he’s singing about. WTF…double-empathy!)
And Dante’s Prayer http://www.youtube.com/watch?v=FDw3CyOmj20 is impossible for me to listen to, at any time, unless I’m totally alone and don’t need to see for a while.
Oh! Two that are hard for me to hear after a breakup are Styx’s Don’t Let It End
and Blue For You by Men At Work.
Styx could never do it for me. Because when I hear Styx, I hear Babe no matter what song they’re singing. And Babe is the polar opposite of a heartbreak song. That was the song my 14 year old self wanted her boyfriends to sing to her. Even now I still sigh at the end. Babe, I love you. . . sigh. . …
One of my bigger breaks ups: Sail Away Sweet Sister
Sail away sweet sister
Sail across the sea
Maybe you’ll find somebody
Who loves you half as much as me
My heart is always with you
No matter what you do
Sail away sweet sister
Always be in love with you
A little odd coincidence, I had a dream about her last night.
Dan Hill’s **Sometimes When We Touch.
**The song is all about a bad breakup, and I was going through one just as it hit the top 40. 34 years, and it still hurts.
**
dante’s prayer is a haunting song…the first time i heard it i thought, hey, what is orthodox music doing in a mckennitt song?! then i read the liner notes and it made a bit of sense. the music is from holy week’s bridegroom service, and fits in with her lyrics. the music for holy week in the russian church is very haunting.
i also agree with dan hill’s “sometime when we touch”, i saw him sing it in concert and the audience was very still during it.
how 'bout enya’s “hope has a place”?
Uh . . . as I was reading this OP, Ann Peebles “I Can’t Stand the Rain” was playing on my iTunes.
Does this mean we’re breaking up , Biggirl?
All you gotta do is sing Babe to me and we’ll be right back together.
On my youtube search for heartbreak songs, I stumbled across The Dramatics living up to their name and then jumping a few miles beyond it with this performance of In The Rain on Soul Train and I just had to share:
Really? I hear Come Sail Away and then I hear Come Sail Away sung by Eric Cartman…
The one I couldn’t stand because of a breakup was Bertie Higgins’ Key Largo, which was all over the charts around the same time.
Looking back on the situation, the breakup was a good thing. She later evolved into trailer trash and the years have not been good to her at all…in fact, she resembles a dried-up old skank.
Serves her right. 
Alone Again, Naturally. Sorry, something just got in my eye…
“Out of Tears,” by The Stones.
“I Can’t Make You Love Me” by Bonnie Raitt. I know it’s more about the narrator’s impending breakup but for me it really brings home the sadness of the end of a relationship.
Alot of that is the emotion she puts into the song. I have been that person and can ::feel:: the heartache when she sings. This song is one of my all time favorite songs ever.
Whitesnake “Here I Go Again”
link to video
Favorite Depressing Songs, a thread by yours truly.
Not quite what the OP described because in the above thread, I ask for songs people do listen to while sad and wallowing in self-pity.