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5 Valentine’s Day Film Picks for the Skeptical Romantic

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Ryan Gosling and Michelle Williams in Blue Valentine

Nate von Zumwalt

Despite its tender origins, Valentine’s Day can haunt lovers with a cloud of expectation. Even more menacing than the prospect of eternal solitude is the feeling that things can only go wrong on such a vaunted day. So call me a cynic, but I challenge you to recall one Valentine’s Day that was so extraordinary, so blissful in straddling the line between cloying romance and exhilarating lust that you would relive, ad infinitum, that one special day with your partner. Sundance suggests a different recourse: cinema. When it comes to romance, film is our portal into worlds that we can’t realistically or even conceivably inhabit. At least that’s my skeptical take. Here are some of our favorites among those fictional (and one real!) worlds. Happy Valentine’s Day.


The Spectacular Now

James Ponsoldt’s third feature effort and third Sundance Film Festival selection is irrefutably his most widely praised, and deservedly so. Sutter Keely (Miles Teller), a well-liked high school senior ever-inclined to live in “the now,” is unceremoniously dumped by his girlfriend. After a night of drowning his sorrows in liquor, Sutter wakes up the following morning next to Aimee Finicky (Shailene Woodley), an otherwise unpopular girl only recognizable for her smarts. Unexpectedly, the two begin to hit it off, opening a new world for Aimee and helping Sutter escape his past one.

The One I Love

“We also had a fantastic time when we did ecstasy, but we’re not gonna’ do that every day of our lives cause you’d die,” says a reserved Ethan (Mark Duplass) to his partner Sophie (Elisabeth Moss) in The One I Love. That’s the disconnect at play throughout Charlie McDowell’s feature debut, a slick dramedy that sees a couple’s faltering marriage galvanized by a trip to a getaway home at the recommendation of their therapist. Soon after their arrival, Ethan and Sophie become privy to some strange happenings in the compound’s guesthouse—a sort of portal into their alternate identities. But like their clashing sentiments towards ecstasy, the pair seems at odds with how to handle the enticing prospect of spending time with each other’s idealized selves. Watch on iTunes.

Blue Valentine

The title really says it all. There is nothing charming nor cheerful about Blue Valentine. Derek Cianfrance’s blunt drama features brilliant performances from Ryan Gosling and Michelle Williams, who play a couple bent on saving their withered relationship. Cianfrance shapes a narrative that shifts seamlessly between diametric stages of a relationship, ultimately portraying the rawest of love stories in a couple’s search for something that may have never existed. If nothing else, Derek Cianfrance is a genius at minimizing Ryan Gosling to a creepy, needy man hiding behind a bushy mustache and a hideous sweatshirt with a giant eagle decal. Watch on iTunes.

Cutie and the Boxer

Whether intentional or not, director Zachary Heinzerling’s debut feature documentary presents the most pleasant of paradoxes. Cutie and the Boxer follows Ushio and Noriko Shinohara, two Japanese artists who meet in New York in the ‘70s and carry on a 40-year relationship that straddles the lines between personal and professional, pleasure and duty. Heinzerling captures their relationship with an authenticity only found in the raw emotions between tailor-made lovers, even if that includes all of the perfect imperfections. Watch in iTunes.

Like Crazy

Drake Doremus’s recent film Breathe In may be the director’s most assured effort to date, but Like Crazy is a stunning antecedent that belongs in the canon of great indie romances. The film summons gut-wrenching performances from two exceptional young actors in this refreshing take on the suffering inherent to long-distance relationships. For her part, Felicity Jones took home a Special Jury Prize at the 2011 Festival, and Anton Yelchin is anything but a slouch.


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