Jack Goes Boating is the story of two vaguely damaged people who get fixed up by mutual friends.
Philip Seymour Hoffman is Jack, a chauffeur for his uncle's limousine service. The woman who takes to him, somewhat unbelievably, is Connie (Amy Ryan), a fragile sales rep for a funeral company. The couple who fix Jack and Connie up are Clyde (John Ortiz), a co-worker of Jack's, and Lucy (Daphne Rubin-Vega), who works with Connie. Clyde and Lucy's marital problems also figure prominently in the plot, the dissolution of their marriage serving as the equal and opposite counterpoint to the energy created by Jack and Connie's hook-up. Clyde and Lucy's half of the story is by far the weaker aspect of the story, which is saying something, in this weak effort about weak people.
The film is Hoffman's directorial debut and based on a play that also featured Hoffman, Ortiz and Rubin-Vega. Hoffman the director has made a film with a standard visual vocabulary, filled with conversations filmed in a shot-countershot manner, often with a rushed pacing that comes from too much cutting back and forth. Hoffman is understandably excited about the ability of film to focus his audience's attention on one face at a time. But his flat angles and narrow focus sap the energy that could have been provided by the performances that pros like he and Ryan are capable of furnishing. His bland montages and corny use of superimposition are far worse trespasses, but they don't interfere too much with the rest of the film.
The play (directed by Peter DuBois) was reviewed positively in The New York Times by Ben Brantley in 2007, who favorably compared Jack to Little Miss Sunshine (both incidentally financed by Big Beach), which might give you some idea of whose cup of tea Jack might be, as well as its level of potency. Brantley called the play a "gentle portrait of pothead losers in love," which makes it sound a lot more fun than it is. Jack Goes Boating exists primarily as a performance piece for a small ensemble that will wring sympathy from its audience for Connie and Jack. We watch because we want them to cement their tentative courtship, and we sympathize—perhaps against our own will—because they border on pathetic.
Jack has a disproportionate obsession with a single song by The Melodians ("Rivers of Babylon," admittedly one of their best) and is working on an unfortunate attempt at dreadlocks. Hoffman the director fetishizes Jack's hair with frequent static shots of the side or back of his head (to perplexing, indeterminate effect). It's a gamble: White Guy With Dreadlocks is probably not at the top of any viewer's list of most sympathetic characters. But because Connie is probably the only chance he's ever going to get at a romantic companion, we can't help but root for him.
Jack's reggae-appreciation is an unfortunate way to color him in. But still, it is a sort of characterization, something that Connie's character does not possess—she exists primarily to be acted upon. Ryan plays a less humorous version of her HR rep on The Office, and she does what she can to fill out Connie, but she's got very little to work with.
So when (minor spoiler) Connie suffers from an incident of sexual abuse, it feels as if Jack Goes Boating is giving a gravely serious issue a troublingly light touch. And the lack of attention her character gets doesn't help (minor spoiler No. 2) the ambiguity of the sex scene toward the end of the film, in which she asks Jack to "overpower" her in order to help her overcome the intimacy problems her attack has caused. I don't mean to say that the film doesn't have the right to suggest Connie might ask for this, just that it short-circuits the complexities of that desire with its lack of investment in making a Connie a fully developed character. Jack Goes Boating attempts to offer a satisfying portrait of two people falling in love. Given its talented two leads, it falls surprisingly short of this modest ambition. And even as it flirts with being outright offensive, it fails there too, dissolving into something far too vague and minor to bother being upset about.