Sebastian (Adrian Grenier) is an introverted, screwed-up member of a dysfunctional upper-class family. He wants to be a writer. He's good-looking, but with so little self-confidence that when a girl seriously likes him, he dumps her. We can guess from an early scene what a confusion his life has been. At a family holiday dinner, we meet his divorced parents, who are both with their new spouses, in one of those uneasy exercises designed to provide continuity for the children, who in fact only want to flee from the table.
His mother Joan (Margaret Colin) is bright, pretty, British, and usually drunk. She's married to a floppy-haired hulk named Hank (Clark Gregg). Sebastian's father, Hartley (John Shea), is an architect with a new Asian-American wife who hardly even seems to be there, so little does she ever say. Then there is Sebastian's sister, Jessica (Marni Lustig), who has a boyfriend on a motorcycle and yearns to climb on behind him and ride far, far away.
Soon after this tortured family event, Hank calls together his wife and stepchildren and calmly announces that he has decided to become a woman. This doesn't go over well. Jessica leaves on the boyfriend's motorcycle, and enrolls at Stanford, which is more or less as far as you can get from Dutchess County in New York. Sebastian listens to Hank's news in stunned silence. Hank wants to remain married to Joan, but she pulls out and moves back to England. At first Sebastian lives with her, but as she recedes into heavier drinking, he moves back in with Hank, who is the only parent who really cares for him. Hank is firm, with traditional values, and sets rules for Sebastian.
This movie might have developed along predictable lines, as a sitcom about coming of age with a transsexual as your parent. But it avoids easy and cheap shots, and actually grows more perceptive and thoughtful, until at last we're drawn in on the simple human level: These are people worth knowing.
Clark Gregg's performance as Hank and Henrietta is the most remarkable element of the movie. No matter what he does with clothing and hair, he looks like a large man in a dress. But there is no simpering, no coquetry, no going for laughs; in his heart he knows he is a woman, and he is true to that inner conviction with a courage that the movie doesn't need to underline, because it permeates the performance. At one point, he has to hit someone to defend his honor; when Sebastian asks him, "Where'd you learn to fight like that?" his answer approaches perfection.
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