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Goofball Answer:

Man,

As a man who's had to sing his way through a few break-ups, I think I can be of some assistance. But you haven't given me much to work with in the way of details here, so I'm going to have to chamber a shell in the ol' advice shotgun and let loose with some pretty broad advice...

Break-ups come in many shapes and severities. But there are songs for any scenario, so I'll run my way through some of the more common break-up states and try to suggest a few tracks that can help ease the pain, bring understanding, fuel the rage, cause reflection on the good times, and whatnot. These aren't in any particular order, mind you, as I'm just throwing 'em down as they come to me. And I'll probably come back to add more, so look for updates to this one.

Get your iTunes username and password ready. Here we go:

Scenario: The wound is still fresh, and denial still hangs nearby.
Band: Yellowcard
Song: Ocean Avenue

Scenario: She dumped you, again. But you'd take her back if she came calling.
Band: The Refreshments
Song: Girly

Scenario: You're in the throes of a break-up, where maybe it could all come back together, and you're searching your heart, because if it comes back together, it'll need some cleaning up.
Band: Third Eye Blind
Song: Water Landing

Scenario: That crazy bitch was always criticizing you, and now you're free.
Band: Fat Cactus
Song: Hawaiian Shirt Song

Scenario: It's been over for a while, but all of the sudden she's calling you again.
Band: Fuel
Song: Shimmer

Scenario: Her parents hated you, and it turns out she was probably ambivalent about you.
Band: Off By One
Song: On My Way

Scenario: She's perhaps moving on to someone new, and you want her to know how you feel about her, even though you know you're not perfect...but close enough.
Band: Fall Out Boy
Song: Grand Theft Autumn (opt for the acoustic version)

Scenario: She travels on business a lot and you think she's dating a Brit on the side.
Band: Third Eye Blind
Song: London

Scenario: She flat-out dumped you for Brit.
Band: Brand New
Song: Jude Law And A Semester Abroad, which is the ANGRIEST break-up song ever.

Scenario: It just didn't have that unidentifiable "glue" relationships need. And you still scratch your head sometimes as to what was missing...
Band: The Kooks
Song: Naive (I really can't figure out what the hell this song is about, but for some reason I know it works here. Funny, eh?)

Scenario: She dumped you and you still feel like you got run over by a truck.
Band: Goldfinger
Song: Counting The Days

Scenario: She doesn't think of you that way, and you desperately wish she did.
Band: The Refreshments
Song: Wanted

Scenario: You broke up a while ago 'cause she moved away. But now she's back in town and you're reflecting on the good times.
Band: Lemonheads
Song: Kitchen

Scenario: You're on the verge of it all collapsing, and you need her to say one genuine thing so you know where she stands.
Band: Snow Patrol
Song: Hands Open

Scenario: You dumped her, because you stumbled upon someone fascinating whom you don't know well yet, but can't stop thinking about.
Band: Boy Kicks Girl
Song: Denny's Girl

Scenario: She surprised you by breaking it off, and you're trying to find yourself again.
Band: Lemonheads
Song: Rudderless

Scenario: There was a break-up, and you're thinking about her, because it's hard not to, but you don't really want to her to know you're thinking about her, except maybe you hope she's hoping you're thinking about her.
Band: Alkaline Trio
Song: My Friend Peter

Scenario: She dropped you out of the blue, perhaps while on vacation.
Band: Matchbox Twenty
Song: Rest Stop

Scenario: Love—honest love—requires vulnerability. And she just never let you in.
Band: The Shins
Song: New Slang

Scenario: She's gone, but she still makes you stir, and you remember what she was wearing when you first saw her, and you want her to know it, badly.
Band: Jack Johnson
Song: Bubble Toes

Scenario: It's on the verge of falling apart, and ending it seems easier than having the difficult discussions.
Band: Yellowcard
Song: Rough Draft

Scenario: It's falling apart, and you're frightened about what the days ahead may hold.
Band: Third Eye Blind
Song: How's It Going To Be

Scenario: It's been a while now, but you'd jump back in immediately if she just said the word.
Band: Dispatch
Song: Out Loud

Scenario: She's gone, and you're a bit angry, but though it won't be easy, you'd still like to make it work.
Band: Better Than Ezra
Song: Sincerely, Me (Get the live version, it's better.)

Scenario: Holy shit it got messy there for a bit. But she is stuck in your head and not moving.
Band: Third Eye Blind
Song: Blinded (When I See You)

Scenario: Things were going OK, but someone else you've known for a while has begun to grow on you.
Band: Lemonheads
Song: Alison's Starting To Happen

Scenario: She dumped you because you seemed detached, or something, and you need her to know how you feel.
Band: Boy Kicks Girl
Song: Little Things

Scenario: She just isn't who you thought she was, and that snuck up on you.
Band: Snow Patrol
Song: It's Beginning To Get To Me

Scenario: You miss her badly, but you can't be that thing she needs you to be.
Band: Everclear
Song: Santa Monica

Scenario: She felt you were only in it for the physical stuff.
Band: Liz Phair
Song: Fuck And Run (This one's for her, not you.)

Scenario: She is never going to let you close again, and it's killing you.
Band: Third Eye Blind
Song: Motorcycle Drive By

Scenario: The two of you are stupid for each other, but can't figure out where you fit in each other's hearts.
Band: Lemonheads
Song: Bit Part

Scenario: She would have been perfect, if only she had let loose a bit.
Band: The Offspring
Song: Want You Bad

Scenario: She'd take you back, if you could just be yourself.
Band: Ani Difranco
Song: As Is

Scenario: She dumped you because you never made her feel special.
Band: Third Eye Blind
Song: One In Ten (This one, again, is for her.)

Scenario: She didn't wait for you while you were in prison (or something similar).
Band: The Refreshments
Song: Preacher's Daughter

Scenario: She dumped you because you cheated on her.
Go listen to some shitty country music, dude.

---

Updates—January 21st, 2010

Scenario: If she's told you once, she's told you a thousand times: it's over. But you don't care; you're in love, dammit.
Band: Teenage Bottlerocket
Song: Crawling Back To You

Scenario: It's over, and that's just as well.
Band: All-American Rejects
Song: Gives You Hell

Scenario: It's ended, but you've still got this dream about the two of you that she just can't shake.
Band: Blues Traveler
Song: Run Around

Scenario: She drove you nuts most of the time. But the breakup hurts. In fact, it hurts badly.
Band: Chevelle
Song: Send The Pain Below

Scenario: You know in your heart it's all salvageable, if she would only open up and talk to you.
Band: Fruit Bats
Song: When U Love Somebody

Scenario: Though you miss her, she did take those annoying habits of hers with her. And that's good.
Band: Spin Doctors
Song: Little Miss Can't Be Wrong

Scenario: You're in that completely-wrecked phase, where you're digging through a box of memories or looking at photos of the two of you over and over again.
Band: The Starting Line
Song: Lasting Impression

Scenario: You suspect she only loved you 'cause you played guitar.
Band: Sara Bareilles
Song: Love Song (Check out the "stripped" version, which is a little more raw)

Scenario: This relationship could be perfect, and she just can't see it!
Band: Quietdrive
Song: Maybe Misery

Scenario: She's getting married (to someone else), but you've still got a thing for her.
Band: Old 97s
Song: Designs On You

---

Updates—January 30th, 2010

Scenario: Things were OK, but you were feeling unimportant, unappreciated, or invisible.
Band: Lemonheads
Song: Being Around (Your first impression here may be to laugh at this one, but listen carefully, and you'll hear the poetic desperation of a man at wit's end. It's actually a tragic and beautiful song.)

Or

Band: Third Eye Blind
Song: One In Ten

~ topher