The To-Do List (2013)
Somehow, "The To-Do List" manages to desexualize sex. If you're lonely on your V-Day, this movie certainly won't make you feel any lonelier. This coming-of-age movie instead packs in enough cringe-worthy scenes to make you want to swear off hooking up forever. Pair those with laughs of the crassest variety, razor-sharp wit, and a reminder of what really matters, no matter your relationship status: friends who have your back.
Drinking Buddies (2013)
This movie is an ode to that college staple that may or may not be the cause of your current emotional state: friends who could maybe, possibly, almost be something more. Kate (Olivia Wilde) and Luke (Jake Johnson) work together, flirt together, and as the title suggests, drink together. They have a few near misses, nights spent in each others' beds with just a little too much frisson to ignore. And who hasn't had that moment with a friend where you held a stare just a few seconds too long?
(500) Days of Summer (2009)
Yes, it's sort of a rom-com. But, as the narrator warns us, "this is not a love story." At its heart, "(500) Days of Summer" is a story of love unrequited, of falling in and out of love, of the tricky turns and swerves of navigating a relationship that's slowly sinking. While parts of it may dredge up painful memories, and others may hit just a little too close to home, when the credits start to roll, you're left with a sense of closure and just a little bit of hope for something, or someone, new.
Sweeney Todd: The Demon Barber of Fleet Street (2007)
If all else fails, turn to the tried-and-true remedy for a broken heart: blood and gore. The Sweeney Todd film adaptation has them in spades, and its dark, depressed atmosphere will match your sad, black heart. Just imagine your person of choice, strapped to Sweeney's barbershop chair and ready for the blade. No? Well, then sit back and enjoy the clever-yet-catchy songs.
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