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Product Description Jack (Academy Award winner Philip Seymour Hoffman, making his directorial debut) and Connie (Amy Ryan) are two single people who on their own might continue to recede into the anonymous background of New York City, but in each other begin to find the courage and desire to pursue a budding relationship. As Jack and Connie cautiously circle commitment, the couple that introduced them, Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega), confront their own unresolved issues, and each couple comes face to face with the inevitable path of their relationship. Based on the acclaimed Off-Broadway play of the same name, this unconventional romantic comedy is a tale of love, betrayal, friendship and grace. Amazon.com Philip Seymour Hoffman plunders social awkwardness for comic effect in Jack Goes Boating. At first, the movie seems like a sad-sack love story: Jack (Hoffman, Academy Award winner for Capote), a limo driver who likes reggae music for its positivity, gets set up with Connie (Amy Ryan, Gone Baby Gone), a trouble-magnet telemarketer, by their mutual friends Clyde (John Ortiz, Fast & Furious) and Lucy (Daphne Rubin-Vega, Wild Things). Connie inspires Jack to improve himself: he starts learning to cook and to swim (so that he and Connie can go boating in the summer to come). But as Jack and Connie take tentative, sometimes clumsy steps toward love, Clyde and Lucy's relationship threatens to collapse from betrayal and jealousy. In the wrong hands, Jack Goes Boating would flounder in angst and sappiness. Fortunately, Hoffman and Ryan always reach for the hopeful (and often humorous) side of their characters, while Ortiz and Rubin-Vega vacillate between tenderness and unsettling bitterness. Hoffman makes his directorial debut with this movie, and his eye for telling social detail comes through as strongly as a director as it does as an actor; Jack Goes Boating's greatest strength is the psychological richness of its characters. --Bret Fetzer