Jack Goes Boating

A shy limousine driver named Jack (Philip Seymour Hoffman), who lives with and works for his Uncle Frank, sets out to win over a blind date, Connie (Amy Ryan), after being set up by her co-worker Lucy (Daphne Rubin-Vega) and her friend Clyde's wife. As Jack strives to perfect swimming and cooking, he begins to get a look behind the veil of his friends' marriage, which is straining under the weight of mutual infidelities. Along the way, Jack and Connie grow closer, and the film builds towards a hopeful conclusion as they walk off into their future together.