Jack Goes Boating

I had no idea that Phillip Seymour Hoffman had such a devoted fan base. Yeah, he won Oscars for his work in Capote and Doubt and he did liven up overrated stinkers like The Talented Mr. Ripley and Magnolia. Still, I was shocked by how many people streamed into the theatre to see his directorial debut, Jack Goes Boating. Nearly all the chairs in the 600-seat space were filled.

Adapted from Bob Glaudini’s play of the same name, Jack Goes Boating revolves around the doings (or, more accurately, not-doings and undoings) of a group of forty-somethings in New York City. The movie opens with limo drivers Clyde (John Ortiz) and Jack (Phillip Seymour Hoffman) discussing Jack’s upcoming blind date with Connie (Amy Ryan), the co-worker of Clyde’s wife, Lucy (Daphne Rubin-Vega).

Connie and Jack are sad sacks, having only their jobs and their relationships with their co-workers cum friends to give their lives any type of purpose. Although Connie and Jack are anxious about romance, the two feel an attraction to each other and embark on a snail’s pace courtship. Jack decides to learn how to swim so he can take Connie on a boat ride the coming summer. (The film begins at the cusp of winter.)

Clyde and Lucy’s long-term marriage is slowly disintegrating under the pressures of sexual betrayal, resentment, and boredom. Lucy is quietly ambitious, railing against her husband’s inertia. Clyde attempts to please her by half-heartedly attending business school. Clyde and Lucy distract themselves from their own unhappiness by coaching Jack and Connie's newly forming relationship.

The four inhabit an urban landscape that is strangely devoid of noise, excitement, or other people. This could have been intentional, a subtle way of depicting the isolation of its characters, but it is an iffy creative choice, forcing the audience to focus exclusively on characters who aren’t fully developed.

The film has other flaws as well. While many of the sly jokes in Jack Goes Boating hit the mark, its glacial pace undercuts the film's overall effectiveness. It takes too long to reap the meager payoff and, like many movies that are based on plays, has entirely too much dialogue.

Jack Goes Boating grated on me for political reasons, too. A woman who is willing to ask for more, Lucy is depicted in a quasi-villainous manner, as she’s the one who breaks the tenuous bond of the foursome. The scene where Connie requests to be “overpowered” by Jack before they have sex wouldn’t have bothered me so much if I hadn’t seen the bloody aftermath of her victimization by a subway pervert earlier in the film… or watched her boss touch her in a highly questionable manner. (Is Glaudini suggesting that some women invite victimization?) And the fact that Lucy and Clyde re-enact the workplace sexual harassment in an impromptu sex game left a bad taste in my mouth.

I did enjoy Jack’s visualization and cooking sequences, though. Exquisitely scored, they have a haunting beauty to them. I also appreciated the defiantly downbeat depiction of a fortyish single woman. Connie is anything but Carrie Bradshaw, and Jack Goes Boating avoids being even remotely similar to a rom-com cliché.

All told, Jack Goes Boating is a grown-folks movie. It doesn’t have a feel good vibe, despite its relatively happy ending, and anyone in search of light fare should skip this thinking person’s romantic comedy.

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