Fired from his teaching job at a posh northeastern finishing school for modeling a brassiere in the teachers' lounge, a high-strung young striver with vague literary ambitions (Paul Dano) drifts into Manhattan in search of self-knowledge. He winds up sharing a cramped apartment with a failed playwright and overbearing misogynist (Kevin Kline) who ekes out a living as an escort for society women. The latter grandly imparts dubious life lessons to the former as the former wrestles with his shameful transvestite urges and his futile attraction to an ecologically conscious coworker (Katie Holmes) with whom he has nothing in common. Based on a novel by Jonathan Ames, this drearily quirky mess wants to be Secretary for submissive males, but it's just a sitcom in a powdered wig and size 17 pumps. Shari Springer Berman and Robert Pulcini directed (108 min.).
Director: Shari Springer Berman and Robert Pulcini
Writer: Robert Pulcini and Jonathan Ames
Producer: Anthony Bregman and Stephanie Davis
Cast: Katie Holmes, John C. Reilly, Paul Dano, Kevin Kline, Alicia Goranson, Cathy Moriarty, Patti D'Arbanville, Jason Butler Harner and Marian Seldes