Two broken souls meet and try to connect in Philip Seymour Hoffman's screen directing debut, "Jack Goes Boating." Hoffman, working from the Bob Glaudini play which he also starred in, conjures up a modern-day "Marty" about fragile, damaged people who might somehow complete one another if they can just surpass the obstacles that this potential romance drops in their way.
Jack is a limo driver working for his uncle in New York. It's a dead-end job, but he's sort of a dead-end guy — quiet, very limited social circle, an even more limited wardrobe. He pulls an ugly stocking cap over his unkempt hair and ruins any illusion his suit and tie might create. His uncle tries to nudge him to find better work. His fellow driver Clyde (John Ortiz) and his wife, Lucy (Daphne Rubin-Vega), want to find Jack somebody. So they set him up. They invite him and Lucy's colleague Connie (Amy Ryan) to dinner.
They're not a charismatic or even very attractive couple. Since Connie works with Lucy at a funeral home, the conversation tends toward the morbid. Jack is shy and doesn't contribute much, and Connie nervously fills the void with prattle. But Connie seems sensitive, and pleased to have the attention of a man who might not be a creep. And Jack, whose devotion to reggae suggests something deep, is touched.
A drunken post-dinner suggestion that the foursome do some boating someday piques Connie's interest. Jack clumsily makes it "a date." It's the dead of winter. He can't swim, much less boat. But they're committed to try their hands at this thing called love, at least until they can get out on a lake in Central Park when the flowers bloom.
Jack has to come out of his shell, learn to swim and figure out how to care about somebody else before this can happen. Connie must overcome the fears and issues that have her well past 30 and single. And both of them have to ignore the example that Clyde and Lucy's less-than-ideal smoke-dope-and-bicker marriage sets for them.
Hoffman keeps his wintry film focused on those four earthy and very real characters. He guards the story's secrets and the actors maintain the contrast between the couples — one struggling to keep going, the other struggling to just make it to summer. There's a hesitance in the way the movie invites us to root for these people, as if it hasn't made up its mind that this is a good idea, either.
Ortiz stands out in this cast, giving Clyde shadings that always surprise. Ryan makes Connie a woman hell-bent on not being an EveryVictim, but tightly wound up in her fears. And Hoffman's Jack plugs along, one of those "quiet types" his friends worry about.
"Jack Goes Boating" is a low-energy romance, a movie that rewards a filmgoer with the patience to let this affair play itself out. Sink or swim, Connie and Jack will come out of this changed. And so will we.