1. Fall Out Boy, “Sugar, We’re Goin’ Down”
A breakup is its own acute misery, but nothing hurts quite like seeing an ex getting physical with someone else. It seems to say, “Because I’m over you, I’m already intimate with this person, and you should feel bad about yourself for not being at this point too.” In Fall Out Boy’s breakout hit from 2005, the narrator is hung up on a woman who treats him as a “notch in your bedpost” (“but you’re just a line in a song,” lyricist Pete Wentz retorts). The second verse describes a scene where he surreptitiously watches her with another guy: “Is this more than you bargained for yet? / Oh don’t mind me, I’m watching you two from the closet / Wishing to be the friction in your jeans / Isn’t it messed up, how I’m just dying to be him?” Considering he’s spying on her from a closet—whose, hers? How did he get there? And why?—the answer to that is “Definitely.”
2. Robyn, “Dancing On My Own”
Throbbing beat and shimmering synths aside, Robyn’s “Dancing On My Own” is one of the most morose songs about hitting the club. A night out takes a painful turn when she runs into her former flame and his “new friend,” who don’t notice her as they make out on the dance floor. She seems to dance not to express herself but to prove to the world she’s all right when in actually she’s “…in the corner / Watching you kiss her.” The next lines, “I’m right over here / Why can’t you see me?” underscore how painful the scene is.
3. Ne-Yo, “Forever Now”
The idea that anyone—even an ex—would betray handsome R&B teddy bear Ne-Yo seems preposterous. However, in his single “Forever Now,” his carefully constructed apologies and amends to a (presumably) estranged partner come crashing down because he catches her doing the unthinkable: “I watch you kiss him softly the same way you kissed me.” The rest of the song details Ne-Yo’s long, slow emotional collapse (“And I scream, ‘What am I gonna do with forever now?’”) as his happily-ever-after fantasy crashes down around him. The strange thing is, it’s not clear whether he’s upset that this particular ex isn’t smooching him, or whether he’s more upset that his carefully constructed future isn’t to be. He’s a little bit clingy, if not obsessive: “All the plans we’ve made don’t work if you’re not around” devolves a few lines later into “I’ll live all my life around the thought of me and you.”
4. Jawbreaker, “Bad Scene, Everyone’s Fault”
The production sheen on Jawbreaker’s major-label album brought Blake Schwarzenbach’s storytelling to the forefront, and in the album’s hookiest song, the singer-guitarist is a shoulder to cry on at a house party. He runs into a friend who “…said his girl had dumped him / And was there with another guy,” though he still liked her. Schwarzenbach’s attention to detail makes the song relatable—from someone blasting Zeppelin to the neon kitchen—and when faced with the sight of his friend’s ex kissing the new guy, Schwarzenbach calls it like he sees it: “They looked good / I mean like in love / Then I remembered my friend.” An argument ensues between the exes, but is thankfully cut short by the arrival of the police. Although being the dumpee is never fun, Schwarzenbach shows being the wingman isn’t easy, either.
5. Dashboard Confessional, “Screaming Infidelities”
If they gave a Nobel Prize for sad-sack acoustic sets about the girl that got away, Chris Carrabba of Dashboard Confessional would be our most distinguished living laureate. In his anthemic ode to a callous ex, Carrabba sings: “I’m missing your bed / I never sleep / Avoiding the spots where we’d have speak / And this bottle of Beast is taking me home / I’m cuddling close to blankets and sheets / But you’re not alone, and you’re not discreet / Make sure I know who’s taking you home.” Maybe the old lady was feeling suffocated, but now she flaunts her newfound sexual freedom while he gets drunk on Milwaukee’s Best. Because she knows that nothing short of a Dresden-level firebombing of his heart will keep him away, the ex makes sure he’s all but in the room with her when she’s getting it on with other dudes.
6. Los Campesinos!, “It’s Never That Easy, Is It (Song For The Other Kurt)”
Over five albums with Los Campesinos!, singer Gareth Campesinos has endured enough sexual humiliation to rival the entire American Pie franchise, but his lowest lows hit on the band’s second full-length, We Are Beautiful, We Are Doomed, a 10-song pileup of passive-aggressive hookups and drunken regrets. This is an album where Gareth confesses to breaking down sobbing while making out with an ex, but even that’s just an appetizer for the ultimate indignity he outlines on “It’s Never That Easy Though, Is It? (Song For The Other Kurt).” In a worst-case scenario, he witnesses his ex-girlfriend—whom he’s still in love with, by the way, as if there was any doubt—“sucking the face of some pretty boy with my favorite band’s most popular song in the background.” It’s a sight that stings his ego as much as his heart. “Is it wrong that I can’t decide which bothers me most?” he wonders.
7. Gin Blossoms, “Found Out About You”
One of the most tragic alt-rock figures in a decade that saw its share, excommunicated Gin Blossoms songwriter Doug Hopkins specialized in tuneful tales about spiraling out of control, none of which cut deeper than the fourth single from the band’s 1992 breakthrough, New Miserable Experience. Reportedly inspired by an ex-girlfriend who punched him in the face after an R.E.M. concert, “Found Out About You” is steeped in painful autobiographical detail, culminating in a stalker-ish final verse as Hopkins obsesses over the betrayal: “You know it’s all I think about / I write your name, drive past your house / Your boyfriend’s over, I watch your lights go out.”
8. The Reputation, “She Turned Your Head”
Neighbors make for convenient romantic partners, but they’re second only to co-workers for the worst exes. Case in point: Living next to an ex—or across the courtyard from one, as singer-guitarist Elizabeth Elmore does in this song—makes her an unwilling witness to his post-breakup life (and whomever that entails). In “She Turned Your Head,” Elmore’s suspicions about a woman are confirmed when her ex starts dating this new person barely three weeks after their breakup. It doesn’t last and their reconciliation seems imminent—until she sees something across the courtyard. “I caught the tail end of her ass slipping up your stairs / And when your light clicked on / I knew you had that bitch in your bed,” Elmore sings. Naturally, she finds it impossible to look away, so she drinks whiskey and stares. “Across the courtyard I kept watch and stopped believing in you.”
9. Airborne Toxic Event, “Does This Mean You’re Moving On?”
The Airborne Toxic Event’s Mikel Jollett doesn’t know when to quit. In the band’s uptempo 2007 single “Does This Mean You’re Moving On?,” Jollett performs several post-breakup no-nos: He calls her at 2 a.m., he bugs her friends, he shows up at her place. While doing that last one, he hears two voices moan and realizes, “Christ, she’s not alone!” That’s a terrible feeling even if the guy did have it coming, but it sends the message. Although Jollett feels “so numb, so swept aside, so dumb,” he still asks a question whose answer is clear to everyone but him: “Does this mean you’re moving on?”