The only real parallel I can think of to this film's style of satire is Evelyn Waugh's Decline and Fall. And in fact both Waugh and Whit Stillman seem particularly galvanized to poke fun at the education system in their respective countries and times - and the faults they reveal about them do not differ that significantly. That is to say that the undergraduates at Seven Oaks College are just as silly and absurd and totally uninterested in actually learning anything in school as Waugh's marvelous bunch of teachers and schoolboys.
This movie, though, is particularly focused on the many and diverse dilemmas of young women at college. It deals with issues like mental illness, sex, friendship, and identity, but all with a very unsettling kind of humor that makes you unsure whether to laugh or offer a serious, sympathetic shake of your head.
Ironically, for a movie that uses title cards to announce new scenes, it absolutely refuses to give you any of the usual signposts - the ones we learn to recognize and follow without even noticing them, the ones that define our interpretations of a character and cue our emotional reactions. Even the timing of scene endings is odd. Through the whole movie, I was constantly surprised by the moments on which Stillman chose to end his scenes, and the new scenes that followed.
For a while, this was somewhat disturbing. But after watching the movie all the way through and thinking about it for a couple of weeks, I've come to really admire Stillman for choosing to disregard convention in every thread of this movie.
The characters seemed at first to be caricatures, and at a certain point I gave up on finding any sane person in the whole movie. It turns out I was right, but the prevalence of insanity eventually turned even the oddest, most absurd characters into sympathetic people. I hesitate a little to say it, but these characters felt more real than the most psychologically dissected protagonist of any modern drama.
Because instead of explaining Violet's OCD or Fred/Charlie's identity crisis or Frank's crippling stupidity, the movie simply presents you with these damaged, multi-layered, sometimes tragic and sometimes hilarious characters, as life presents you with equally complex and incomprehensible people. In real life, you don't get revelatory back stories or cues about who's going to end up with whom or who's going to crack under the pressure of being human or who's going to find a happy ending, if anyone ever does.
There's something both unsettling and deeply comforting about this movie, both for regular people and for storytellers. It shows that you can break all the rules and still come out with something good, maybe even better. It's not a flashy, presumptuous movie. It probably won't have much popularity because it's not easy to watch, but I wholeheartedly recommend it. Even if you don't fall in love with the characters or sympathize with the unique challenges of East Coast college life, it's fun to take a break from formulaic summer blockbusters and get your assumptions shaken up a little bit.
It'll also give you a whole new appreciation of rainbows.