An itinerant city story centering on an aging wiseacre and his wilting dreams, Loveless opens with Andrew (Andrew von Urtz) laying some casual game on a woman in a bar. The scenes that follow suggest laissez-faire is a way of life: He is casually late for work at his generic office job, where he practices casual sexual harassment before casually insulting his friends at a party. Director Ramin Serry has a lock on the dissatisfied New York City coaster with big, abstract plans and a deflective way with a punchline; his grasp on what lies behind that persona is less assured. Though an old flame (Cindy Chastain) resurges and Andrew’s first film is finally getting traction, his former, sloppier life is only a half-step behind. A typically impulsive night out connects him with Ava (Genevieve Hudson-Price), a lithe downtown brat with a pack of overprotective siblings. Obsessed with their dead dad, soon they’re obsessed with Andrew, too—a baggy subplot that threatens to take the story in three different directions but suddenly settles on a fourth. Despite inventive moments between the performers, the central character, true to his type, is too casually drawn to sustain our interest in whether he loves or loses.