Jack Goes Boating

Philip Seymour Hoffman directs and stars in this New York-set black comedy drama adapted by Robert Glaudini from his own stage play. Jack (Hoffman) is a shy and socially awkward limo driver whose married friends Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega) set him up on a blind date with the equally shy Connie (Amy Ryan). The two begin a tentative and gradual courtship that gives a whole new meaning to the word patience.

But as Jack and Connie overcome their isolation and begin to open up to one another, the marriage of the friends who brought them together begins inexorably to fall apart.