Jack Goes Boating is an unconventional romantic comedy set in the midst of working-class New York City life.
Based on the acclaimed Off-Broadway play of the same name, Jack Goes Boating stars John Ortiz ("Pride and Glory"), Daphne Rubin-Vega (Broadway's "Rent"), Amy Ryan ("Gone Baby Gone") and Philip Seymour Hoffman ("Capote"); with Hoffman making his feature directorial debut on the film. Bob Glaudini adapted his own play for the screen.
In the dead of winter, we meet Jack (Hoffman), a limo driver who has vague dreams of landing a job with the MTA, a mild obsession with a reggae song, and has begun a half-hearted attempt at growing dreadlocks.
He spends most of his time hanging out with his best friend and fellow driver, Clyde (Ortiz) and Clyde's wife Lucy (Rubin-Vega).
The couple set Jack up with Connie (Ryan), a co-worker of Lucy’s at Dr. Bob's Funeral Home in Brooklyn. 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 wants.
But as Jack and Connie cautiously circle commitment, Clyde and Lucy's marriage begins to disintegrate. From there, we watch as each couple must come face to face with the inevitable path of their relationship.
Starring: Philip Seymour Hoffman, Amy Ryan, John Ortiz, Daphne Rubin-Vega