10 Messed Up Movies For A Cozy Winter First Date

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Second date not guaranteed.

first date

It’s getting cold which means you really don’t want to go outside for a first date. All of those layers ruin a perfectly good outfit, you have to struggle through freezing temperatures. And then there’s the chance the person you’re meeting is a total dud. Who has the time, especially with the holidays fast approaching.

So, instead of struggling through the snow, we’ve put together a list of some first-date movies that’ll help you decide if this person matches your sick tastes, or if it’s time to swipe left. It’s the ultimate test for their sensibilities, and perhaps their stomachs. Reader beware: this may result in a new love interest ghosting. Don’t say we didn’t warn you.


Ah, Midsommar. The best worst date movie there is. Ari Aster’s nightmarish odyssey into Scandinavian hell is all about a horrible, devolving relationship in the face of human sacrifice. It features an incredible performance from Florence Pugh as Dani, one half of the relationship, who’s dealing with the death of her parents and sister. She goes on vacation with her boyfriend Christian (Jack Reynor) and his buddies as a distraction. They head to a remote village in Sweden for this midsummer celebration. Too bad their hosts have other plans for these tourists. Nothing sets the tone for a future relationship like Pugh’s cathartic screaming and man in a bear suit set on fire. Watch Midsommar on Prime Video.


This is a film I showed each of my high school boyfriends to see if they could hang. Honestly, it didn’t go as poorly as I expected but I blame teenage boy hormones and the promise of getting to second base. In a nutshell, the film follows a young woman who discovers through a traumatic sexual experience that she has vagina dentata, or a toothed vagina. But it’s more than just a girl biting off penises. It’s a nuanced portrayal of getting power back from the men who wronged you. But it’s also pretty nasty, especially for people with a penis. Watch it on Prime Video, Tubi, Vudu, and Pluto TV.

The Human Centipede 2: Full Sequence

Of course there’s a Human Centipede movie on this list. Nothing sets the mood for a date like watching people get sewn ass to mouth. The second one gets a spot on this list because, well, it’s 12 people instead of three. While Teeth has nuance, The Human Centipede 2 does not. It’s all about the shock and disgust of it all. If your date likes this one, you may actually want to ghost them. But that one is up to you. Rent it on YouTube.

Capture Kill Release

In Capture Kill Release, the couple that kills together, stays together. In Nick McAnulty and Brian Allan Stewart’s 2016 film, a couple plots to murder a strange purely for the thrills. But it all goes awry when the man decides he can’t go through with it. Usually it’s the female counterpart of the relationship shown feeling guilty. But not in Capture Kill Release. Nothing scares a male partner like the possibility of going on a love-fueled murder spree! This hidden gem is also found footage, which makes the violence on screen feel all the more real. Watch it on Tubi.


Don’t let that title deceive you. Todd Solondz’s 1998 film will not bring you happiness. On the surface, it seems very cheery. But that sunshine exterior is thanks to Solondz’s very dark sense of humor. The film follows three sisters and the strange connections they have through their everyday lives. Happiness boasts an incredible ensemble cast, including the late Phillip Seymour Hoffman, Jane Adams, Jon Lovitz, Laura Flynn Boyle, Dylan Baker, and more.


Lars von Trier has a rather warped perspective on love that runs throughout all of his films. One of his most, or least, romantic films is the Kirsten-Dunst-vehicle Melancholia. It’s both a dour look at marriage and a film about the end of the world. Relationships fall apart, Earth is obliterated, all incredibly uplifting stuff, especially for a first date. But hey, if you both like it, you’ll have plenty to talk about afterward. Watch it on Pluto TV, Tubi, and Vudu.


Speaking of von Trier and romance, if you really want to up the ante, then opt for his body-horror nightmare Antichrist. It opens with a black-and-white sequence of Willem Dafoe and Charlotte Gainsbourg having sex while their toddler son plummets out of a window. It only gets worse from there as the grieving parents head to the woods for some peace and quiet. But when they arrive, dark secrets are revealed and very bad things happen to genitalia. This one is like a date on expert mode, especially if you’ve just started dating. But what’s a date without a little bit of risk and vulnerability about the twisted movies you like? Rent it on YouTube.

Visitor Q

Takashi Miike is a prolific Japanese director who doesn’t shy away from the more extreme side of the horror genre. His 2001 film Visitor Q is no exception and is often described as an erotic black comedyhorror film. In Visitor Q, a mysterious stranger visits a rather dysfunctional family made up of a perverted father, an abused mother, a son being bullied, and a daughter who’s a sex worker. The stranger then proceeds to infiltrate the family, seducing each of them in the process. It’s all about the weird, taboo sex in this one, which may or may set the mood for romance. Watch it on

Megan Is Missing

Nothing gives off first date vibes like a found footage movie about the abduction and death of two young girls! Amy and her best friend Megan are polar opposites, with Amy maintaining youthful innocence while Megan chooses to party and spend much of her time with older men. When Megan meets a supposed classmate online, she starts a digital romance with him. But when they meet, Megan goes missing. NAME tries to find her friend but her sleuthing doesn’t go as planned. It’s incredibly sad and disturbing, especially with the victims being young girls. The film recently went viral on TikTok as users watched the film and recorded their reactions. It serves as a rather harrowing look at the dangers of digital relationships, which may leave. strange taste in your mouth if you met your date on an app. So, proceed with caution! Rent it on Prime Video.


I told my dad’s wife to watch this on an airplane once and I almost got disowned. That’s a pretty good indicator of just how bizarre and uncomfortable Yorgos Lanthimos’ 2009 film is. The film follows a Greek family with a controlling patriarch who doesn’t want his three children to ever leave their compound. He teaches them the wrong words for things and bends them to his will. He also hires a woman to come sexually satisfy the son. Yup, you read that right. It’s an incredibly disquieting film about abuse, incest, and finding liberation from abuse. You may find you and your date inching further and further away from each other as the film progresses. Watch it on Tubi.

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