Just when you thought the "awkward" genre had altogether vanished after the trail of feel-good uncomfortableness left by (500) Days of Summer, Juno, Garden State, et. al., Whit Stillman has brought it back in spades with Damsels in Distress. Known for his stark and satirically protracted storylines (as with The Last Days of Disco and Metropolitan), Stillman centers his plot around an unusual group of girls focused on "youth outreach" at the college campus they attend. At times, it is difficult to discern what the film is actually supposed to be about, but, if nothing else, you've at least got Aubry Plaza as "Depressed Debbie" (I guess anyone named Debbie always has to be a downer) prattling on about the definition of being clinically depressed, not to mention a cameo from Arrested Development's Alia Shawkat as an angered student named Madge.
A fundamental rule of watching a Stillman movie is surrendering to the notion of an alternate, politer universe. In the one inhabited by Violet Wister (Greta Gerwig) and her posse of obedient acolytes, Rose (Megalyn Echikunwoke) and Heather (Carrie MacLemore), the objectives are simple: 1) Date less attractive, less intelligent people, 2) Start a new dance craze, and 3) Effectively run the Suicide Prevention Center. As for the first tenet of Violet's group, well, Violet sums it up best when she states, "Do you know what's the major problem in contemporary social life? The tendency to always seek someone cooler than yourself."
Perhaps this belief of Violet's is why she chooses to take a new transfer student by the name of Lily (Analeigh Tipton, who you recognize from America's Next Top Model and Crazy, Stupid, Love) under her wing. Slightly gawky and less polished than one would expect to fit into Violet's crew, Lily is immediately fascinated by Violet's strange world of impossible rules and aspirations. While others, like Lily's friend Xavier (Hugo Becker, whose accent is equally as arduous to understand as it is on Gossip Girl), view Violet as a pretentious bitch, Lily finds something admirable about her quest to fulfill her dreams not just for the campus, but for herself as well. In this regard, there is something very Rushmore-esque about the film.
At the first party Lily attends with Violet, Rose, and Heather, Violet explains that her boyfriend, Frank (Ryan Metcalf), is neither exceptionally attractive nor intelligent, but that she feels that it's her job to "take a guy who hasn't realized his full potential--or doesn't have much--and then help him realize it... or find more." Upon arriving at the party, Violet takes up with Frank on the dance floor, shouting--in a completely non-ironic way--"I love a golden oldie!" about 90s dance hit "Another Night" by Real McCoy.
As Lily grows closer to Violet, she also grows closer to Xavier, much to the dismay of his girlfriend, Alice (Meredith Hagner). After Xavier blatantly expresses jealousy over Lily's current suitor, Charlie (Adam Brody, whose real name turns out to be Fred when we discover he lies about his identity to mask the fact that he has been attending Seven Oaks University for eight years), Alice ends the relationship--leaving the, ahem, back door wide open for Xavier to pursue Lily. In the meantime, Frank has sent Violet into what she refers to as a "tailspin" (as opposed to simply depression) after cheating on her with one of the girls she was helping at the Suicide Prevention Center.
As the plot progresses to the end of the second act, everything seems to stall as relationships turn incestuous and then revert back to how they were--followed by the random insertion of a musical number at the conclusion. But hey, they had to segue into the Sambola!, Violet's dance craze, somehow. So I suppose that if you feel you haven't taken away anything from Damsels in Distress, you can't deny that it has improved your ballroom skills.