Jack Goes Boating is a tale of love, betrayal, and friendship set against the backdrop of working-class New York City life. Jack and Connie are two single people who on their own might continue to recede into the anonymous background of the city, but in each other begin to find the courage and desire to pursue their budding relationship. In contrast, the couple who brought them together, Clyde and Lucy, are confronting the unresolved issues in their rocky marriage.

The multifaceted Philip Seymour Hoffman makes his directorial debut demonstrating an assured style and grace, both behind the camera and in front of it. He leads a skilled cast, who waltz through their group scenes in perfect counterpoint, each getting what he or she needs from the other. The writing is fiercely authentic as are the performances. Lyrical and lovely, Jack Goes Boating is an offbeat love story that almost forgets to happen.