Jennifer Carpenter, Kristen Connolly and Alexander Poe star in a comedy about three New Yorkers struggling to uncover the truth behind their romantic entanglements. Disheartened by his latest relationship catastrophe, Graham (Poe) attempts to rekindle the spark with his ex-girlfriend, Laura (Connolly). In the attempt to win her back Graham discovers he has a unique problem: Laura and another one his ex-girlfriends (Carpenter) are dating the same guy.

35-year-old Morris Bliss (Michael C. Hall) is clamped in the jaws of New York City inertia: he wants to travel but has no money; he needs a job but has no prospects; he still shares an apartment with his widowed father; and the premature death of his mother has left him emotionally walled up. When he finds himself wrapped up in an awkward relationship with Stephanie (Brie Larson), the 18-year-old daughter of a former classmate, Morris quickly discovers his static life unraveling and opening up in ways that are long overdue.