There’s a long tradition of films about awkward, damaged people who find in each other the acceptance and comfort that the rest of the world has denied them; it’s an old fantasy, though it seems that in the era of mumblecore and emo, the characters just keep getting more awkward and damaged. There are echoes of everything from The Fisher King to Punch-Drunk Love in Philip Seymour Hoffman’s subdued directorial debut, Jack Goes Boating, but screenwriter Bob Glaudini—who adapted his own play—finds a few particularly touching grace notes in the familiar dynamic.
Hoffman stars as the eponymous Jack, a meek, shambling New York limo driver with a love of reggae music and an essentially nonexistent romantic history. When his best friends, John Ortiz and Daphne Rubin-Vega (reprising the roles they played opposite Hoffman onstage), set him up with equally meek, strange Amy Ryan, they discover that while they’re both eager for a connection, they have little to talk about, and no social graces to smooth their way. After fumblingly discovering that Ryan would like to go boating come summer, Hoffman decides to learn to swim. And so begins a process of minor self-improvement, as he tries to shore up the tentative bridge he and Ryan are building toward each other. Meanwhile, Ortiz and Rubin-Vega are actively—and increasingly obviously—burning their own bridges.
It’s never fully clear what these two things have to do with each other; there’s a vague nod toward the symmetry of one relationship possibly starting while another seems to be ending, and an equally vague sense that Hoffman can take his friends’ dissolving relationship as a cautionary tale. But the story largely lacks a theme or a sense of causality; when it abruptly morphs into a reeling, yelling John Cassavetes drama, it feels more like a reach for third-act excitement than an organic story outgrowth. Ryan’s underdeveloped character comes perilously close to being a Depressive Pixie Dream Girl, a passive quirk-collection with little personal agency or energy. But the performances are strong, and Glaudini pulls the story forward largely on the sweet image of an adult gladly taking baby steps into a new world. Hoffman’s largely prosaic direction becomes lyrical and textured in those moments, as his character all but hypnotizes himself with the minor exotica of trying new things. The film could stand to get that far into his head more often; Jack Goes Boating tells a tender story reasonably well, but it rarely lets viewers feel the emotions instead of thoughtfully observing them.