XO, X-NO: Best Cinematic Breakups


‘Tis the season, people. Romantic devotion is being forced down our throats at every franchised big box store and shop carrying Ivanka Trump’s wares. It’s the utterly un-ignorable VALENTINE’S DAY, and yet, you don’t have to care about not having a paramour to hold hands with as you waltz down the Seine. Why? Because this year, you have movies. Actually, none of us need anyone anymore. We all have movies. And the oddly comforting boops of our Rokus.

Fuggheddabout what you’re supposed to be doing on Tuesday (boning someone very successful in a Kiki de Montparnasse garter), and take yourself to the movies instead. In the meantime, please, enjoy this roundup of the best breakups on film.

And no, The Notebook is not on this list, because I’m not YOUR SHEEP!!!


“I really loved meeting you tonight…but maybe we should take some time off from each other. It’s not you, it’s me.”  

While this isn’t technically a breakup scene, it certainly is grounds for a restraining order. Poor Jon Favreau, 6 months fresh off of his debilitating breakup, and still completely inept at communicating with women. One of the most nail-biting attempts at courtship perhaps ever committed to celluloid, there is something both terrifying and tranquilizing about watching such an obsequious display of neuroses from a sweaty, lonely guy in a wife-beater on his 90s home phone.


Eternal Sunshine of the Spotless Mind

“I can’t see anything that I don’t like about you.”

This film is one long break-up scene, and Charlie Kaufman nailed what it is to sleepwalk, both horrified and enchanted, through your own amorous history. Kaufman pokes, prods, and provokes the confines of temporal sense in this film as we see the inimitable Joel and Clem meet, realize they’ve already been in love and been made to forget one another, and then go backwards so we can see them fall in love for the first time, all while grasping to avoid their memory-destroying procedures. With Michel Gondry’s deft and tender hand, it manages to be the opposite of higgledy-piggledy, with a structure that weaves us in and out of each character’s heart ventricles with the dexterity of a 16-year old Russian dancer on pointe.

Clem: “And in your wormy little brain, you try to figure out, “Did she fuck someone tonight?”

Joel: “No, see Clem, I assume you fucked someone tonight. Isn’t that how you get people to like you?”


Social Network

“There’s a difference between being obsessed and motivated,” Jesse Eisenberg (as Mark Zuckerberg) asserts to his beleaguered girlfriend in Social Network’s electric opening bar scene.

Appropriately, my favorite factoid about Social Network is that on his first week on set, Jesse Eisenberg approached David Fincher with a handwritten list of his personal favorite takes of each scene. Eisenberg was a total newbie, and Fincher tried not to laugh in his face. Eisenberg quickly learned that he didn’t get to pick which of the myriad takes Fincher notoriously demands from his actors and crew that he had the power to eventually choose. But – as telling as that opening line – it’s a bold, weirdly socially inept quirk that heavily hints as to why he was chosen for the role of genius-isolationist Mark Zuckerberg, a character who is, according to the Social Network script, at least, questionably high on the spectrum.

“Well, I want to try to be straightforward with you and let you know that we’re not dating anymore. Dating you is exhausting, dating you is like dating a Stairmaster. You’re going to go through life thinking that girls don’t like you because you’re a nerd. And I want you to know from the bottom of my heart that that won’t be true. It’ll be because you’re an asshole.”

A searing turnaround in 5 minutes, we see how impossible it is to converse with Zuckerberg and how earnestly Rooney Mara’s Erica tries, eventually overwhelmed with the barrage of un-subtly layered insults he volleys her way. A truly stellar breakup scene – even though we were all exhausted of him before even she is, and that’s only a handful of minutes into the film.


Forgetting Sarah Marshall

“Why don’t you just put on some clothes, and we can sit down and discuss this?”

Most of all, this scene is memorable for two key visuals: the specific bachelor-hood of eating Lucky Charms out of a massive silver mixing bowl, either because the other bowls are all dirty or because he needs to be able to shovel an entire box’s worth of cereal in at one sitting (both equally pitiable) and for the full-frontal male nudity we’ve all been due in a breakup scene.

“I’m not going to put clothes on. I know what that means. If I put clothes on, it’s over.” And so he sits down, naked on the couch, with the body of someone who eats Lucky Charms out of mixing bowls, ready to calmly discuss why she’s breaking his heart. Good breakup scene, but great breakup movie.


Wet Hot American Summer

Wet Hot American Summer is a double-hitter in that it contains perhaps two of the most perfect breakup scenes of all time. One: humiliatingly curt and careless that could only spring from a pre-pubescent playground breakup or Paul Rudd’s Neolithic character Andy, and the other, a thoughtful, debilitatingly detailed reasoning for choosing the hot guy over the nice guy.  

“You taste like a burger. I don’t like you anymore.” Paul Rudd is here to remind us that the most shallow of humans roam the earth, breaking beautiful, fragile hearts hither and thither, with such arbitrary impressions as to suggest that the next lay is just around the corner, so this one is inherently expendable. See what I mean? Just, stay home and watch movies.*

Brokeback Mountain

“I wish I knew how to quit you.”

This scene takes on a supernatural patina of melancholy now that Heath Ledger no longer lopes across our silver screens. Based on an Annie Proulx’s short story originally published in The New Yorker in 1997 (!!), Ang Lee’s molasses-slow, naturalistic film adaptation culminates in this mournful scene, bursting with frustrated desire for a different kind of life, one filibustered by fear and social convention.

Unfortunately (?), my own personal memory of this film is superseded by its sequel, the real-life movie in which my uncle went to get a colonoscopy shortly after the film’s release and at the crucial moment, apparently cried out to the doctor “I WISH I KNEW HOW TO QUIT YOU,” disrupting the procedure.



“He tastes like you but sweeter.”

Speaking of colons, Julia Roberts is brutally interrogated by Clive Owen in this gut-wrenching breakup scene, when Roberts confesses that she’s been having an affair and Owen insists on knowing the brutal “fucking cave-man” details of her extramarital sex life.

This movie is one long, near-suffocating breakup beautifully directed by Mike Nichols, as we watch four beautiful, outrageously captivating people love, fuck, and betray one another. Clive Owen’s Larry says what a part of us all wants to say when we’re smack in the middle of being simultaneously abandoned and betrayed by a lover: “Don’t say it. Don’t you fucking say “You’re too good for me.” I am, but don’t say it. You’re making the mistake of your life. You’re leaving me because you believe that you don’t deserve happiness, but you do.”


Blue Valentine

“Tell me what to do. Tell me what I should do. I’m gonna get better. You just gotta give me a chance to get better.”

Cruel, cruel world. A movie so brutal and beautiful and heartbreaking that you’ve gotta be some kind of masochist to see more than once. This scene takes place in a sumptuous editing pas-de-deux between the present-day dissolution of their marriage and the day they got married at City Hall, all dumbstruck in myopic love, with no clue of what lay just ahead of them. It’s a searing metaphor for love – the requisite foolhardiness of moving forward with feeling, the necessity of ignorance of what the future holds. The blue naiveté of young valentines.

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