Honour student Shirley (Katherine Waterston) gets entangled in an affair with her babysitting client, Michael (John Leguizamo), in The Babysitters. (Peace Arch)It’s been nearly a decade since American Beauty made the suburbs the preferred spitting grounds for the smuggest type of indie filmmaker. In The Babysitters, all the anti-outskirts signifiers sit in their boxes, waiting to be ticked: the summer lawns hiss provocatively; the houses are little boxes made of ticky-tacky; everyone is slumped, soul-sucked, over the wheels of their SUVs. What lies beneath is lust, only sometimes bridled, and a moral sludge worse than the landfill under everyone’s feet.

Sixteen year-old Shirley (Katherine Waterston, daughter of Sam) is a gangly bookworm with a low-grade obsessive-compulsive disorder. When babysitting, she can’t help but get down on her hands and knees and scrub the kitchen floor with bleach. It is said position, perhaps, that causes middle-aged Michael (John Leguizamo) to first take note of his sons’ babysitter’s more fetching qualities. He offers to drive Shirley home, to another suburb far from his stultifying bourgeois existence and harpy wife (played by poor Cynthia Nixon, trying to make something substantial out of the wispy cliché of the working-mother ball-buster).

Michael is lonely and professionally unfulfilled, and thereby the newest member of the leghold-trapped Men in Turmoil club. His slot is right next to Jason Bateman glumly strumming his electric guitar in Juno, which is next to Kevin Spacey lifting weights in American Beauty. It takes a Noxzema-fresh young girl for these men to imagine the lives they think they deserve to be leading.

Katherine Waterston's 16-year-old Shirley ends up running a prostitution ring of neighbourhood babysitters. (Peace Arch) One of Juno’s cleverer tricks was pshawing the sympathetic, aging, man-child figure; Bateman proved a loathsome narcissist, but his wife was hardly the materialist yuppie he made her out to be. That’s a rare turn in the teen-meets-midlife-crisis narrative; these guys usually get to be heroes, even as they victimize.

Always an interesting actor, Leguizamo lends Michael a brimming good-guyness, but he is far too sympathetic for what comes next. Two outsiders comforting each other turns into a sweaty, ongoing affair, punctuated with guilt money. After each romp, Shirley adds to the stack of cash under her mattress. It’s her own, unique college fund, and she soon loses her sweetness and becomes just another upwardly mobile American tucking into her piece of the pie. Michael’s friends get wind of his arrangement, and Shirley completes her downslide, playing Heidi Fleiss and pimping out her teenybopper friends for a cut of the action.

Director David Ross trains a fisheye lens on the proceedings; there’s something not quite real about the look of The Babysitters. Shirley organizes her “dates” via Google Calendar, but otherwise, the girls have the long, flat hair and flares of retro babes, like the evil teens in Carrie. This un-reality means the film lands like a fairy tale; it’s more allegory than outrage, and that esthetic feels way too soft for the material. The Babysitters exists in that same American Apparel-grainy universe as Sofia Coppola’s (far superior) '70s period piece, The Virgin Suicides. Those sepia tones, and that love of creepy nostalgia, seem to be the favoured palette of so many young directors, from Wes Anderson to Noah Baumbach. But all the pretty irony only dilutes The Babysitters; it should be much uglier.

The darkly comic tone Ross is straining for is really only achieved in the high school setting, where all the energy that keeps the mean girls’ dynamic churning gets channeled into the prostitution ring. The other girls give Shirley her percentage by sliding envelopes through her locker door. Competition brings out business cards, then bitchiness, then baseball bats. The striving, mercenary push for middle-class success — college, college, college! — gets nicely deflated.

An age-appropriate teen suitor (Spencer Treat Clark) suffers a major crush on Shirley, but his clumsy attempt at a kiss only drives her farther away. They’re living in different worlds, which is the power sex has in high school, maybe especially with girls. Sex can catapult a kid into adulthood, as it does Shirley, who looks at this awkward boy like he’s a totally foreign creature. Waterston is a promising actor; she’s unaffected, with a strength behind her blushing baby cheeks.

The Babysitters obviously wants to bat viewers out of their comfort zone, and it will be interesting to see if anyone is outraged by lines like, “Paid fellatio is not that much more humiliating than flipping burgers.” But a film that could have said something about contempt for young women ends up showing them massive contempt itself.

Meanwhile, the girls’ fathers, teachers and male “employers” get off scot-free, simply doing what they have to do to break out of the suburban blandness inflicted on them by their wives. Not strong enough for satire, the film hovers above real wryness, and gets dangerously glib. Denigration and heartbreak aren’t laughable just because they don’t occur downtown.

The Babysitters opens in Toronto, Montreal and Vancouver on May 9.

Katrina Onstad is the film columnist for CBCNews.ca.