Jack Goes Boating (2010): C-

A character study whose two protagonists don’t resemble human beings but intricately assembled screenwriter constructions, Jack Goes Boating proves an inauspicious start to the directorial career of Philip Seymour Hoffman, who also stars in this adaptation of Bob Glaudini’s 2007 play. Hoffman previously presented Glaudini’s work at New York City’s Joseph Papp Public Theater. Yet despite his familiarity with the material and his natural efforts to expand the story in cinematic ways, there’s still a persistent stagey quality to this tale of Manhattan limo driver Jack (Hoffman), a mopey schlub always hiding his scraggly braided hair under a wool cap, who’s afforded a rare shot at happiness when his married best friends Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega) set him up on a date with Lucy’s funeral home sales team co-worker Connie (Amy Ryan). Given that Connie is a despondent, hesitant, slightly weird loner, she’s a perfect match for Jack, who Hoffman embodies as an awkward, heavyset man made small by his internalized personality.

Their romance is predictably clumsy and tentative, though their shared kindness, yearning for companionship, and search for “something positive” (which is Jack’s description of his beloved reggae music) slowly bridges their social-retardation chasm. Meanwhile, Clyde and Lucy serve as the story’s counterpoint, their marriage crumbling under the weight of past infidelity and the resentment, anger and self-loathing that lingers in its wake. Hoffman helms his portrait of two relationships heading in opposite directions with sensitivity and restraint, affording adequate space for the characters’ tightening or fraying bonds to develop gradually, and free of blunt expository explanations of the tumultuous feelings bubbling under the surface. Spurred by twin offhand comments by Connie, Jack sets off on dual self-improvement quests – to learn to swim so that he might take Connie boating in the summertime, and to learn to cook so that he might make her dinner – that express his urgent desire for togetherness and reciprocated warmth, and the lengths he’s willing to go to achieve those ends by winning over his new girlfriend.

Alas, from Jack’s visualization routines, habit of clearing his throat when he’s nervous, and swim lessons under Clyde’s tutelage, to Connie’s multiple, questionable claims of being sexually assaulted – which, along with her third-act request for a pseudo-rape bedroom fantasy, speak to the pleasure and pain of male-female relations – Jack Goes Boating carries an overpowering scent of writerly affectation. Habitually staring off into nothing with looks of misery and fear tattooed on their faces, and accompanied by a soundtrack insistently placed in the action’s foreground, Jack and Connie don’t resemble recognizable flesh-and-blood individuals but merely amalgams of italicized tics, hang-ups and gestures designed to represent various themes. Both freak out, fumble and brood in such meaningfully quirky ways that they never resonate as real people. Their courtship is one about isolated strangers finding comfort and joy in a discovered soulmate, but they consistently come off as unbelievable fictitious creations – brought to life by Ryan and, especially, Hoffman via mannered quiet voices, cautious comportment and pained scrunched-up expressions – conveniently gravitating into each other’s idiosyncratic arms.

Which is a shame, since in Clyde and Lucy, Hoffman’s behind-the-camera debut provides a polar-opposite view of romance that’s rooted in compellingly credible human experience. To be sure, Glaudini’s scripting of the spouses’ tense rapport also carries with it a strong theatrical aroma, regardless of the fact that Hoffman branches his story out to include more locations than were featured in the original play. Nonetheless, in Clyde’s efforts to deal with an imagination run wild thanks to Lucy’s unfaithfulness, and in Lucy’s increasing disdain for her ambition-challenged husband, Jack Goes Boating delivers glimpses of drama rooted in recognizable emotional and psychological reality, charting the way relationships mutate and disintegrate with a reasonably astute eye. Unfortunately, the finale’s hash and alcohol-fueled roundelay of miserabilist histrionics conclusively exposes the mechanical story’s stagey roots. Yet more pressing still, in its moderately rending investigation of Clyde and Lucy’s tattered love, the film suggests it would have been better off repositioning its supporting figures to lead-character status.