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Anti-Valentine’s Day Movies for Cynical Cinephiles

By David Young · February 13, 2023

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You don’t have to be with someone in order to be happy. Singleness isn’t an affliction, but sometimes we need reminding that relationships are a breeding ground for problems: jealousy, sabotage, and maybe even murder, in some cases. Valentine’s Day is often a time for couples to celebrate each other, but single people don’t need to protest in silence. Instead, binge some favorites in cinema that really show how love isn’t always everything it’s cracked up to be. The films below each give a good reason — some tamer, some more frightening — as to why you should be happy where you’re at, with or without someone else in the mix. Let’s dive into these hand-picked anti-Valentine’s day movies.

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My Best Friend’s Wedding

First up on our list of anti-Valentine’s day movies is My Best Friend’s Wedding. Jules is struck with the news that her best friend and on-off lover of many years, Michael, has found someone. She’s even more shocked when she learns he’s ready to marry, which wakes up a realization: She loves him and can’t let this happen. The bride-to-be offers another surprise by asking Jules to be the maid of honor, inspiring her to take every opportunity for sabotage to get her man back. No matter how you look at this movie, it’s a case study of love versus friendship — and what happens when the two seemingly collide.

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Get Out

Fear is a real mood killer, that’s for certain. And yet, black photographer Chris Washington slowly falls into the pit trap of an unsettling visit with his white girlfriend’s family. The first-time jitters are increased by racial comments, strange behavior, and the creeping realization of something very amiss with the people in Rose’s family and their social circle. If you ever experience a relationship or a family like Rose’s, chances are you should get out as soon as possible. For anyone already single, this movie is solid proof of why trusting others can be hard.

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Why spring for real-life love when you can have something more perfect? Her answers that question, showing a writer whose loneliness brings him to an unlikely solution: AI. Samantha, a system designed to be the perfect companion, shows up for Theodore in a big way, and he starts to treat her as a girlfriend — only to learn the hard way that a relationship, even one like this, has its drawbacks. Theodore’s own feelings for Samantha come into question for their validity as much as their real meaning, showing us all that what we call “love” isn’t always as simple as we think it should be.

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John Tucker Must Die

It’s time for payback in this punchy comedy classic. No one can really argue that John Tucker’s womanizing had hurt quite a few people, but who would have guessed he’d get it back in spades? As his exes plot to set him up for heartbreak, John’s feelings are tugged around quite a bit, reminding many of how brittle, harsh, and disappointing romance could be — especially in our school days.

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Black Swan

It’s not hard to see why Black Swan stands out as a representation of all that’s difficult in trust, romance, and sex. No matter which way you look at it, the film covers each of those topics with a grim understanding — like sex working as a tool for manipulation within the story at hand. Most of this demanding performance of a film screams “Don’t trust anyone,” until you get to the meat of the story. And let’s be perfectly clear: Nina’s world and the things she sees and feels are categorically not what they seem. In fact, some of the more dramatic bits may not be real at all — which would surely make anyone feel a bit more alone in the world.

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The powerhouse classic of all-time cinema, this love story gone awry tells you many things about the world. Namely, that love can be selfish, selfless, or cruel. It also shows that Rick didn’t have a complete heart of stone — he let the love of his life leave him for the good of the cause. You already know the iconic ending, which leaves you with an important message: Being together isn’t always the right thing.

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The Lobster

The way things go down in dystopia always gives you a bit more perspective. That remains true for The Lobster, a movie where people are joined by tradition to seek companionship or risk being turned into animals. This ritual search is disturbing and relatable in many ways, as it compares our current dating world to the bizarre situation contrived by law in The City. Singleness, in many ways, is a promise of freedom from that bizarre ritual. If there’s ever a time to scrutinize the oddities of dating through the eyes of a fictional world, V-day just seems like the right time!

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500 Days Of Summer

Watching a past relationship rise and fall is a bit morbid but fascinating nonetheless. That’s what makes 500 Days of Summer a compelling choice for an anti-Valentine’s Day movie. After all, it’s got everything: chemistry followed by frustration, and attachment followed by heartbreak. If that’s not what this is all about, we don’t know what is!

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Sometimes, relationships wind up bringing out the worst in you. That’s all the more the case when your significant other doesn’t care about your feelings and puts themselves first. If you need to see something like that up close, check out Midsommar. Time and again, Dani puts her trust in a boyfriend that doesn’t acknowledge her needs, and the new dangers of their trip to a rural commune bring them all the closer to the end of their relationship — as both their boundaries and sanity become blurred by the midsummer festivities.

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Read More: Funny Valentines: Rom-Coms to Make You Laugh and Fall in Love

Love doesn’t conquer all in these movies. In fact, something else always takes precedence, be it revenge, freedom, friendship, or even the world’s safety. What’s important, though, is that each one teaches you a relationship isn’t the end-all, be-all. If you’re celebrating being single, each of these movies gives you a concrete reason for that celebration. Keep your eye out for these anti-Valentine’s day movies and others that show what makes singleness such a great thing when you have it.

Read More: Why Romance is the Perfect Subject for TV Shows

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