Jack (Philip Seymour Hoffman) is a lonely and shy New York limo driver who works for his uncle. He has not had much experience dating and has anxiety attacks when things don't go as he’s planned. To calm himself, he plays Bob Marley's reggae classic "Rivers of Babylon." It usually works. Jack's interest the Rastafarian path has prompted him to grow some dreadlocks and smoke marijuana.

Jack’s best friend and coworker Clyde (John Ortiz) is going through a mid-life crisis in his marriage to Lucy (Daphne Rubin-Vega). He has hopes of a better life and is taking a business course; she works at a Brooklyn funeral parlor run by Dr. Bob (Tom McCarthy) who has a side business selling self-help tapes to other morticians. Feeling sorry for Jack, Clyde and Lucy set him up with Connie (Amy Ryan) who also works at the funeral parlor. She is apprehensive about men and has had several bad experiences, so she’s relieved when she meets Jack and realizes he is gentle and vulnerable.

The relationship between these fearful misfits begins very slowly. When Connie tells Jack in the middle of the winter that she would like to go boating on the lake in Central Park, he realizes that he will have to learn how to swim in case something bad happens. Clyde volunteers to teach him the basics, and they spend quite a bit of time at a local pool. Jack really gets off on the art of visualizing a positive outcome to his efforts.

Then Connie hands him another challenge: she has never had anyone except her mother cook her a special dinner. So Jack begins to take culinary lessons from the head pastry chef at the Waldorf Astoria Hotel. However he’s rattled when Clyde confesses to him that Lucy had a prolonged affair with this man. Given his idealistic appreciation of his friend's marriage, this news is something he would have preferred not to hear. Jack wonders whether he and Connie will be able to navigate the tricky waters of an intimate relationship.

Assaulted by a man who rubbed up against her on a subway, Connie goes to the hospital. Jack brings her a stuffed koala bear and then lets her listen to the soothing sounds of his favorite anthem: "Rivers of Babylon." They both look forward to the dinner party where Jack will share his culinary treats in a sumptuous meal.

Jack Goes Boating, a story about four working-class middle-aged people trying to remake themselves (even the laid-back Jack has applied for a job with the MTA), marks the directorial debut of the immensely talented actor Philip Seymour Hoffman, with a screenplay by Bob Glaudini, adapted from his Off-Broadway play. As would be expected from such talented people, this oddball film is a beautifully acted, character driven drama about love blooming and the sad crumbling of a marriage in its last stages. Whereas other writers or directors might have patronized these fragile individuals and their yearning for a brighter and better life, Glaudini and Hoffman honor their blue-collar aspirations. We found ourselves rooting for Jack and his pursuit of perfection in swimming and cooking. We winced each time he nervously cleared his throat as a sign of his anxiety or fear of what was happening to him. We were also moved by Clyde's toxic jealousy and Lucy's looking for a fresh start outside of her marriage. We felt for the most vulnerable character of all, fearful Connie who dreams of sexual satisfaction but doesn't feel up to it.

Jack Goes Boating starts quietly and ends with an explosive finale built around the dinner party. In his debut as a director, Philip Seymour Hoffman continues to demonstrate his knack for excellence: this is one of the Best Films of 2010!

Special features on the DVD include Jack's New York; "From the stage to the big screen"; and deleted scenes.