“This is me sitting with Greta Gerwig, who plays Lola, in the smallest New York apartment in the history of filmmaking. It cannot be more than 500 square feet. After Lola gets dumped by her fiancé, she moves back into this tiny studio across from the projects in the East Village. This is where she puts herself together.”

“In any long-term relationship,” says 28-year-old writer-director Daryl Wein, “there’s a struggle to be independent.” He should know: Wein and his girlfriend and screenwriting partner, Zoe Lister-Jones, have been on and off for eight years. Codependence is something the pair have mined for delicate comedic effect in both their 2010 indie film Breaking Upwards and their upcoming movie, Lola Versus. Greta Gerwig plays Lola, 29, a Ph.D. student whose fiancé, Luke (The Killing’s Joel Kinnaman), breaks things off without warning just before their wedding. Suddenly Lola is alone, with only her best friend (Lister-Jones) and her free-spirited parents (Bill Pullman and Debra Winger) keeping her afloat.

What follows draws from Wein’s and Lister-Jones’s experiences during their periods apart. “I wanted to make a relationship movie that feels true to our generation,” he says. Wein has also made a distinctly New York film. Lola’s lessons in solitude take place all over the city—from the High Line in the Meatpacking District to Brooklyn’s Vinegar Hill. “I feel almost obligated to shoot in New York,” says Wein, who lives in Brooklyn and whose Twitter account identifies him as “white, Jewish, and scared”—not unlike the persona of a certain celebrated New York filmmaker. “I very much look up to Woody Allen,” says the young auteur, who embraces the challenge of carrying the torch of nebbishy, neurotic comedy. “This film is in the style of Annie Hall, except it’s not a love story between a guy and a girl—it’s the love story of a woman who’s learning about herself.”