GRADE: B+

Academy Award winning actor Philip Seymour Hoffman’s directing debut is a funny and occasionally intense adult seriocomedy about a painfully shy New York limo driver who’s the object of his best friend’s matchmaking efforts, and the impact those efforts have on the friend’s precariously perched marriage.

Jack (Hoffman) is a quiet, pot-smoking, Reggae loving introvert in his early forties. His best buddy, Clyde, a fellow limo driver, is a genuine pal whose authentic affection and big-brotherly love for Jack is obvious. Clyde’s wife, Lucy (Daphne Rubin-Vega), works with Connie (Amy Ryan), a socially-challenged, withdrawn woman she thinks would be the perfect match for Jack.

Both Jack and Connie are open to the idea of meeting, and so a casual date is arranged. That dates goes well and an instant rapport develops between them. She tells Jack she’d love to go boating some day and that no one’s ever cooked for her. Clearly smitten, Jack promises to fulfill both wishes even though he can’t swim a lick or cook so much as a hamburger.

Clyde pitches in by offering to teach Jack how to swim, which results in some of the film’s warmest and most winning scenes. At the same time, Lucy contacts a friend of hers—a famous chef who agrees to tutor Jack on how to prepare a simple yet elegant gourmet meal.

Complications begin to surface in all four directions after Connie is roughed up, punched and psychologically shaken by a passing scoundrel and Clyde tells Jack that the chef was once Lucy’s lover; a two year affair that took place during their marriage. Each of these developments reveals unresolved issues that threaten to boil over, pushing Jack Goes Boating beyond the boundaries of a simple romantic comedy.

The contrasting storylines in Bob Glaudini’s incisive screenplay, based on his off-Broadway play, performed on stage by the four leads, give Jack Goes Boating a dynamic structure—the spectacle of a new couple forming while another faces dissolution serving to magnify the beauty and chaos at both ends of the spectrum.

Everyone acquits themselves exceedingly well, with Ryan, who excelled as the drug addicted mother of a kidnapped child in Gone Baby Gone, a particular standout. The locations are minimal, the presentation personal, the style sporadically cinematic, but each of these qualities is exactly what’s called for in a heartfelt story like this, which is why Jack Goes Boating is so interesting and entirely entertaining to watch.

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