JACK GOES BOATING is a quiet, closely observed social drama about the lives of real people, people like you and me. And the unfortunate realization that occurs 10 minutes into the film? Real people are super, duper boring.
Philip Seymour Hoffman's directorial debut—in which he also stars—follows a few months in the life of Jack, a chauffeur in Boston with a fondness for reggae that manifests in a really unfortunate head of white boy dreads. Jack is close friends with his fellow driver Clyde (John Ortiz), and Clyde's hot-in-a-realistic-way wife, Lucy (Daphne Rubin-Vega). But Clyde and Lucy's problems are soon evident, and it's not long before stories of infidelity emerge, much to Jack's chagrin. Clyde and Lucy's marital problems highlight Jack's relative inexperience—he's never been in a long-term relationship, and so he doesn't understand that open hostility and infidelity go with the territory, the couple tell him. (The fucked-up emotional logic of this argument provides an early clue as to where Clyde and Lucy's relationship might be heading.) Meanwhile, Lucy introduces Jack to Connie (Amy Ryan), a nervous, uncomfortably intense woman who seems a magnet for negative male attention, at least until Jack comes along.
Against the backdrop of his friends' marital collapse, Jack struggles to make himself a man worthy of Connie, and a quiet romance unfolds between the two odd, awkward people. It's nice to think that odd, awkward people will find each other and pursue odd, awkward lives, listening to reggae and talking about how their boss sexually harassed them and doing internet research into how to grow white person dreads. And it's nice to think that the reliably great Hoffman thinks that it's important to shed light on the lives of odd, awkward people. But this character study of the dull just doesn't make compelling cinema.