The problem with "cool parents"—the kind who give their children all the space they need to express themselves—is that their kids often turn out obnoxiously self-centered, convinced that they've been brought up in a special way because they are special, and superior to normal folk. In Amnon Buchbinder's Whole New Thing, two "follow your bliss" environmentalists realize one day that their precocious 13-year-old son Aaron Webber can write an elaborate fantasy novel, but can't do math, or relate to people his own age. So they send Webber to the local public school, where his androgyny and arrogance rattle his classmates and draw the attention of his depressed English teacher, Daniel MacIvor. The middle-aged MacIvor gets so revitalized that he tosses the lame juvenile novel he's supposed to teach (Snowboard Snowjob!) and goes with Shakespeare instead.
With its narcissistic, not-as-sharp-as-he-thinks-he-is juvenile hero and weird approach to bridging the generation gap, Whole New Thing plays a lot like Wes Anderson's Rushmore, only sober instead of whimsical. Also, Whole New Thing's May-October friendship is more of a romance. Webber develops a major crush on MacIvor, and although MacIvor is gay, he prefers anonymous encounters in remote public restrooms to statutory rape. But it's a delicate dance for MacIvor, as it is for Webber's parents. Webber's folks are the kind who celebrate their son's first wet dream by sharing their own stories of sexual awakening, and MacIvor doesn't want to crush the spirit of an outsider who's got it tough enough already.
Initially, Buchbinder and his co-screenwriter MacIvor hammer too hard and too squarely on Webber and his rarefied family life. The kids' parents (well-played by Rebecca Jenkins and Robert Joy) are having marital trouble, because they've discovered they aren't as committed to free love as they thought they were. And Webber comes off as an impossibly blinkered little twerp. But Whole New Thing develops its story slowly and carefully, nearly always opting for the plausible over the sensational. It isn't subtle, but it's appealingly assured and aware of its limits, like a precisely written short story. In the end, Buchbinder and MacIvor move the plot to a final line—"I have no idea what he's dreaming about"—that perfectly sums up the paradox of parents trying to force their children to be free spirits.