Bob Glaudini’s Jack Goes Boating, known mostly from its initial production turned into a film directed by and starring the late Phillip Seymour Hoffman, was staged at the Paradise Factory in the East Village by The Seeing Place company in an intimate, almost too detail-filled production directed by Erin Cronican.. Directed by Philip Seymour Hoffman. 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. But as Jack and Connie take tentative, sometimes clumsy steps toward love, Clyde and Lucy's relationship threatens to collapse from betrayal and jealousy. History. His friend and co-worker, Clyde, and his wife Lucy, feel sorry for Jack … In the wrong hands, Jack Goes Boating would flounder in angst and sappiness. Jack is a quiet, reserved, shy, and lonely man. In Philip Seymore Hoffman's directorial debut, Jack Goes Boating is an unconventional romantic comedy set in the midst of working-class New York City life. Jack Goes Boating premiered Off-Broadway in a Labyrinth Theater Company production on March 18, 2007 at Martinson Hall at the Joseph Papp Public Theater. Daphne Rubin Vega during "Jack Goes Boating" New York Opening Night - March 18, 2007 at B Bar in New York City, New York, United States. Jack Goes Boating is a 2007 play by Robert Glaudini.It is an unconventional romantic comedy set in the midst of working-class New York City life. Laced with cooking classes, swimming lessons, and a smorgasbord of illegal drugs, Jack Goes Boating is a story of date panic, marital meltdown, betrayal, and the prevailing grace of the human spirit. Directed by Philip Seymour Hoffman. He dreams of becoming a driver for the MTA but they remain unfulfilled. Jack Goes Boating Synopsis: Jack is a shy and awkward man who drives a limo and lives an unassuming life. 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). With Philip Seymour Hoffman, Amy Ryan, John Ortiz, Richard Petrocelli. Production. With Philip Seymour Hoffman, Amy Ryan, John Ortiz, Richard Petrocelli. by Joel Benjamin . Chris Noth and Eric Bogosian during "Jack Goes Boating" New York Opening Night - March 18, 2007 at B Bar in New York City, New York, United States. Jack Goes Boating premiered off-Broadway in 2007 at the … A limo driver's blind date sparks a tale of love, betrayal, friendship, and grace centered around two working-class New York City couples. After "Jack Goes Boating" with Connie, then Jack can go music shopping with the embalmer's assistant and find a new song that describes their new life together, since his Rastafarian pretensions is a thing of the past. JACK GOES BOATING is a slow character study based on a stage play. A limo driver's blind date sparks a tale of love, betrayal, friendship, and grace centered around two working-class New York City couples. Philip Seymour Hoffman, who also directs, plays Jack, a down-on-his-luck limo driver in New York City. There isn’t much of a plot to Jack Goes Boating.