He is Jack’s self-conscious heart. The title, you see, is a metaphor, for oddball Jack deciding it’s time to open up and experience something of the world, such as learning to swim and going on dates. His friend Clyde (John Ortiz: Public Enemies) sets up Jack (Philip Seymour Hoffman: The Invention of Lying), with Connie (Amy Ryan: Changeling), a coworker of Clyde’s wife, Lucy (Daphne Rubin-Vega); the irony is that while Clyde and Lucy seem “normal,” their marriage is actually secretly falling apart from neglect, and that while Jack and Connie seem “weird,” they are in, fact, more grounded and eager to make their strange new romance work. Hoffman makes his directorial debut here, working from a play by Robert Glaudini, and finds some lovely ways to look at working-class New York, where the guys work as limo drivers and the gals for a creepy grief counselor; there’s a harsh, cold, perfectly apt anonymity to how Hoffman depicts a city where it can be tough to be on your own. But the oddball-ness of Jack and Connie is strained and — excellent performances by both actors aside — fails to ring true. And the tale of these two couples has a shaggy-dog aspect to it, building, ever so intractably, to a conclusion that feels so inevitable and anticlimactic that one wonders who considered the story worth telling in the first place.
