[A portion of this is adapted from a review of the book Restless Virgins: Love, Sex, And Survival At A New England Prep School, by Abigail Jones And Marissa Miley, for a blog back when the book came out in 2007].
On March 9th, Lifetime premiered Restless Virgins, its TV movie adaptation of the book about the Milton Academy sex scandal, which, as a highly fictionalized take on a book that was a distorted interpretation to begin with, is nothing like anything that has ever existed in real life.
Sutton Academy, the movie's version of Milton, is a place where wealth, athletic ability, and debauchery reign supreme. Milton Academy, where I went to both middle and high school, is an academic octagon where athletics are encouraged as a way to pad your college transcript and a freakish number of students graduate without getting laid.
As with all cartoonish depictions of prep school, Restless Virgins depicts a school ruled and defined by those who have money, and of all the things this movie gets wrong, from the Gossip Girl-style uniforms (the only non-athletic uniforms that existed at Milton were unofficial and clique-based, hence the girls known to some as "The J. Crew") to the raging pep rally (the most beloved sport among students was intramural dorm soccer, often played in kilts), this take on wealth is the laziest. It's easy to paint the super-privileged as hateful brats, and some are, but as much as their wealth does often make them infuriating, it's not because they're overt and snobbish about it -- but because they're totally oblivious.
While the mascots of young wealth in this country are usually people like Paris Hilton, Blair Waldorf, or those terrifying brats that used to be on My Super Sweet 16, New England wealth—wicked old money—is an entirely different animal. Since it's rarely depicted accurately anywhere (including Gossip Girl), it's worth attempting to clarify here.
As depicted in countless films, books and TV shows, the super rich are spoiled trust fun kids who turn their nose up at us for shopping at Target and driving Fits. Images of ye olde John Hughes movies still ring true today, with the "Richies" tormenting our financially-challenged heroine just because she doesn't live in a mansion and her dad is Harry Dean Stanton (which should make her the queen of the school, but whatever).
New England/Mayflower rich people like the ones I went to school with don't quite work that way. They don't really mock the poor, because they never interact with them; they'd never be snobby about your used Focus because they don't know what that is and don't understand why you don't just buy a Range Rover like the one their dad got them for their 15th birthday (until they crashed it and got it replaced with a Lexus).
People that have had money for generations don't really have a perspective on how much money they have, especially when they grow up with other rich kids, are educated alongside more rich kids, and then either go to work for the family biz/their friends' dads they've known since their days at the country club pool. The more noble sort use their wealth to do something righteous and money-losing, like start a sustainable organic dragonfruit farm near their private expanse of Maine coastline or host a few ex-gangbangers as artists in residence on the family island off of Martha's Vineyard.
While my family was by no means poor, our money was newer and far more Jewish, which is to say it was earned through years of sacrifice and hard work, and never shown off or spent frivolously, lest the secret police come in the night and kill the children, rape the women and steal all the silver (as they did near my grandfather's village before his family escaped from now-Lithuania when he was a boy).
Not only was I aware of how much money we had, I was raised to always feel nervous about it, so, while my parents would never skimp on education, they believed strongly in living below your means. I know there are Jewish kids now that have $5 million bar mitzvahs where Li'l Wayne performs and everyone gets a motorcycle as a parting gift, and while that's more in line with the old money goyish kids I used to know, that's not how my parents' generation would roll, even if they had that much money (and even then, they'd probably still describe themselves as "comfortable").
Of course, we all sometimes get bitter about those who have more money, trust fund kids, Trumps, etc. but for every minute you spend judging someone based on their obscene wealth, they spend absolutely no seconds acknowledging your existence, let alone making fun of your poverty. And who knows, I might be remembering my experience wrong, but of all the things I was made fun of for in high school, and they are legion, driving a ten-year-old junker, wearing thrift clothes and not having a second home in St. Barths were not among them.
There are a lot of reasons to dislike the book Restless Virgins, but even more to hate the TV movie and dismiss it as Gossip Girl of the North. Someday, somebody will accurately depict the New England prep school experience, but, shockingly, Lifetime won't be the ones to do it.