Jack Goes Boating is a tale of love, betrayal, friendship and grace centered around two working–class New York City couples. The film stars John Ortiz (American Gangster), Daphne Rubin–Vega (Broadway’s “Rent”), Amy Ryan (Gone Baby Gone) and Philip Seymour Hoffman (Capote), with Hoffman making his feature directorial debut. Bob Glaudini (“A View From 151st Street”) adapted his acclaimed Off Broadway play for the screen. Essentially, Jack (Philip Seymour Hoffman) and Connie (Amy Ryan) 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 that introduced them, Clyde (John Ortiz) and Lucy (Daphne Rubin–Vega), are confronting unresolved issues in their marriage. Jack is a limo driver with vague dreams of landing a job with the MTA and an obsession with reggae that has prompted him to begin a half–hearted attempt at growing dreadlocks. He spends most of his time hanging out with his best friend and fellow driver Clyde and Clyde’s wife Lucy. The couple set Jack up with Connie, Lucy’s co–worker at a Brooklyn funeral home. Being with Connie inspires Jack to learn to cook, pursue a new career and take swimming lessons from Clyde so he can give Connie the romantic boat ride she dreams of. But as Jack and Connie cautiously circle commitment, Clyde and Lucy’s marriage begins to disintegrate. From there, we watch as each couple comes face to face with the inevitable path of their relationship.