Philip Seymour Hoffman, ever the critic’s darling, takes a hand at directing in Jack Goes Boating. Unsurprisingly, he seems to be doing what he does best: telling stories of people with simple, relatable problems. The film follows two couples navigating the pitfalls of modern relationships. Hoffman stars as Jack, who is introduced to Connie (Amy Ryan), by way of his friend Clyde (John Ortiz). Jack, a New York limo driver with dreads an affinity for reggae, cautiously approaches his potential new romantic relationship with Connie. His learning to swim seems to be a major component of the process. Complementing Jack and Connie are Clyde and Lucy (Daphne Rubin-Vega), whose marriage is precariously close to falling apart. The film comes from writer Bob Glaudini, who adapted his play for the film’s screenplay.