Top 5: Romantic movies for the disaffected

Valentine’s Day is an arbitrary holiday designed to exploit relationship insecurities to prop up the floral and greeting card industries… so let’s try to undermine the holiday while still celebrating it. Yay, it’s Valentine’s Day on Sunday!

Romantic comedies tend to tell milquetoast, often sociopathic stories based in Hollywood ideas romance; you can find plenty of them on our Romance Pinterest board. A few dare to go someplace weirder, darker, or less satisfying than the typical meet-cute story, and we’d like to highlight five standout examples. We briefly considered featuring some more nihilistic movies like Blue Valentine or Lars von Trier’s Antichrist and Nymphomaniac, but we’re sticking with the ones you could still honestly call romantic comedies.

Paul Thomas Anderson’s collaboration with Adam Sandler famously gave the Grown Ups star a place to show his acting range beyond his usual man-child roles. The central romance story is equally sweet and unsettling, involving extortion from a phone sex line and pudding-related airline scam.

Not many romantic comedies deal with death to the gleeful extent of Harold and Maude. Young Harold’s obsession with death and repeated mock suicides drives him into the arms of an elderly woman who helps him appreciate life. Critics derided the movie on its release for its overwhelmingly dark humor.

Her staged a love story between a lonely man and an artificial intelligence. Lars and the Real Girl has Ryan Gosling romancing a sex doll. Though similar to Her in its outline, this is a decidedly sillier film but no less sentimental about the concept of love.

A film about a man in the doldrums of his career reconnecting with an old fling at a high school reunion sounds like old hat, but John Cusack’s protagonist is a hitman. This is by far one of the most violent romance movies ever filmed; it all builds to a blood-soaked subversion of the typical proposal scene at the ending.

We have to spoil this one: Celeste and Jesse divorce, and by the end, they have overcome their discomfort and amicably separate. It’s extremely easy to mine failed relationships for endless will-they-won’t-they tension (let’s throw shade at How I Met Your Mother for this). In Celeste and Jesse Forever, the filmmakers are more honest about what would happen.

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