In an apartment on Manhattan a couple of friends from the New York upper-class meet almost every night to talk about social mobility, play bridge and discuss Fourier's socialism; the cynic Nick, the philosophical Charlie, party girl Sally and austenite Audrey. They are joined by Tom. His background is much simpler and he is critical of their way of life. But he finds a soul mate in Audrey, who without his knowledge falls in love with him.
It's the Christmas season, which coincides with the deb ball season in New York City. Most of the world outside of the upper class or who aspire to such a life are not aware that these deb balls still exist. After one such dance, Tom Townsend, by chance, is invited to a small home gathering of a small clique of ball attendees who call themselves the Sally Fowler Rat Pack (SFRP), with one of them, Charlie Black, further coining their life with the acronym UHB (urban haute bourgeoisie). Tom now lives largely outside this world, ever since his parents' split four years ago, he living with his mother, while his remarried father, with who be believes he has a good relationship despite not seeing him often, is the one with the wealth. In addition, Tom has a mentality different than the others, he who is quietly straightforward almost to the point of being socially unaware, does not believe in the deb ball life despite never having been part of it, and believes he can have valid opinions on matters without ever having experienced them. Tom and most of the SFRP have mutual acquaintances, most specifically Serena Slocum, Tom's ex-girlfriend who most can see with who he is still infatuated. Despite these issues - the lack of money of which they are aware - and despite having internally mixed feelings about Tom as a person, the SFRP invite him to join their group to balance out the genders. He is taken under the wing of the group's alpha male, Nick Smith, who truly likes Tom, but has an open dislike for Rick Von Sloneker, Serena's current boyfriend, Rick and Serena who are not part of the SFRP. Although they travel to the balls and follow-up parties as a group, Tom is to be the official/unofficial companion of Audrey Rouget, the insecure one of the group who knows more about Tom than she lets on. As the deb ball season progresses and nears its end, the questions become if the SFRP life can continue as is or if the individual members even want it to continue.
A group of young upper-class Manhattanites are blithely passing through the gala debutante season, when an unusual outsider joins them and stirs them up.
- In New York City, upper class socialites return home from college for Christmas break, which coincides with debutante ball season. After attending one of the balls, Princeton student Tom Townsend (Edward Clements) is ushered into a taxicab by Nick Smith (Christopher Eigeman), who mistakenly assumes Tom was trying to hail the same cab. Nick and his friends, known as the "Sally Fowler Rat Pack" or "SFRP," introduce themselves and invite Tom to an after-party at Sally Fowler's (Dylan Hundley) parents apartment on the Upper East Side. There, Tom admits he never uses taxicabs, and Nick guesses that he is a "public transportation snob." However, Tom, whose parents divorced three years ago, is simply short on cash since his wealthy father remarried.
Tom talks to Audrey Rouget (Carolyn Farina) and her best friend Jane Clarke (Allison Parisi), who went to the same boarding school as his ex-girl friend, Serena Slocum. Audrey and Jane reveal that Serena, who had many suitors, read her love letters aloud. Audrey recalls Tom's letters, in which he expressed disdain for debutante society. Tom admits he is still opposed to it, and only attended tonight's ball out of boredom.
Charlie Black (Taylor Nichols), an intellectual who pontificates endlessly on the state of the "preppy" class, accuses Tom of being a hypocrite. Charlie asks about Tom's political leanings, and he claims to favor a model of socialism developed by French philosopher Charles Fourier. Charlie argues that Fourierism failed. Sally invites Tom to another party the next night, but he declines.
However, after going to bed after dawn at his divorced mother's apartment on the Upper West Side, Tom wakes up in the early evening and finds the tuxedo rental shop closed when he tries to return his tuxedo. Jane Clarke telephones him, complains of an "escort shortage," and persuades Tom to accompany Audrey Rouget to tonight's party. Tom puts his rented tuxedo back on and joins the group.
At the black tie party at the Plaza Hotel, Serena Slocum (Elizabeth Thompson) arrives with her new beau, a titled aristocrat named Rick Von Sloneker (Will Kempe). Nick Smith detests Von Sloneker and denounces the titled aristocracy as the "scum of the earth." Audrey talks to Tom about her favorite books. When she mentions Jane Austen's 'Mansfield Park', he is taken aback by her preference for such a "notoriously bad" novel. Later at Sally's apartment, Charlie Black tells the group they are all doomed to "downward social mobility," along with the rest of the preppy class. Nick promises to put Tom's name on the "floor committee" for the Christmas ball, but Tom reiterates that he does not plan to attend any more dances. Nick guesses Tom is declining because he is short on money, and convinces him all he needs is the proper formal-wear. Nick agrees to go shopping with Tom, who buys the tuxedo he has been renting for a reduced price.
Tom remains preoccupied with Serena, despite Audrey's obvious interest in him. Another night later, he talks to Audrey about his estranged father, whom he sees very little because his stepmother does not like house guests. Audrey brings up Mansfield Park again, and Tom admits he never reads novels, but defends his right to form opinions based on literary criticism.
At another ball at another hotel, Charlie laments the word "bourgeoisie's" negative connotations, given the bourgeoisie's contributions to society. While waiting for Audrey outside the restrooms, Tom encounters Serena, who tells him she and Rick have broken up. Tom agrees to escort Serena home, and asks his drunken friend, Fred Neff (Bryan Leder), to tell Audrey he will return. Unfortunately, Fred is so drunk that he does not remember what Tom said to him. Fred ends up vomiting on another party guest and has to be taken home.
Tom escorts Serena home and kisses her goodnight her apartment. Later, he finds the SFRP back at Sally's apartment. Audrey, who never received Tom's message via Fred, is upset that Tom disappeared. Charlie, who harbors a secret crush on Audrey, reprimands Tom for abandoning her and calls him an egoist. The next day, Audrey makes excuses for Tom's behavior, but Jane warns her to be careful. Audrey argues that Tom is the only boy she has ever liked, and she refuses to give up on him despite "apparent inconsistencies."
That night, as Audrey forgives Tom for running off to deal with Serena, Charlie discusses the term he has invented to describe the preppy class: Urban Haute Bourgeoisie, or "UHB." Cynthia McLean, who used to date Rick Von Sloneker, asks Nick to explain why he hates Rick so much. Nick recounts the tragic story of Polly Perkins, who committed suicide after Von Sloneker convinced her to take part in a degrading sex act with multiple boys. Walking home with Tom, Nick admits he invented "Polly Perkins," but claims she was a composite of real people.
On Christmas Eve, Jane warns Audrey that Tom still has feelings for Serena, and Audrey wanders around the city depressed. She runs into Serena at a church service and cries while singing hymns. Tom spends Christmas Eve alone at his mother's apartment.
Two days later on the day after Christmas, the SFRP reunites to play bridge and strip poker at Jane's parents apartment. Tom tells Audrey he went to see his father on Christmas, only to discover he had moved to Santa Fe, New Mexico. Tom predicts he will be disinherited, and also mentions he has been reading Jane Austen's 'Persuasion' and surprisingly likes it. Later, Nick and Cynthia take mescaline and Nick becomes paranoid.
During a parlor game called "Truth," Jane asks Tom to reveal his romantic interests in descending order. Tom only names Serena, and predicts he will give up on romance for a while if things do not work out with her. Audrey leaves the room. Charlie tries to console her by proclaiming his affection, but she runs away. Nick is the only one of the group to attend The International, a televised white tie debutante ball that the others watch on TV at Jane's apartment. Jane invites Rick Von Sloneker over, and when Nick returns from the ball, Von Sloneker confronts him about the Polly Perkins story that he just found out. Nick admits Polly was a fake name he used to protect the identity of Cathy Livingston. At the mention of her name, Von Sloneker loses his temper and claims he had nothing to do with Cathy's suicide. He punches Nick, breaking his nose. In the early morning, Nick gives Tom his top hat, asks him to watch over the SFRP, and boards a train to visit his estranged father as well as return to college.
That evening, Tom takes Serena to dinner at an expensive restaurant. She offends him when she admits to throwing away her old love letters. However, she recalls that Audrey, who was a fan of Tom's letters, asked to keep them for herself. Realizing he has feelings for Audrey, he sets out to find her, only to discover that she and Cynthia have snuck away to Rick Von Sloneker's house in Southampton, Long Island.
When Jane leaves to go on a date with a guy from another college, Tom joins Charlie and Fred at a bar, where they meet and talk with an older preppy guy who rejects Charlie's theory that the UHB are doomed to failure. After Fred leaves the group go home (having just quit drinking and gotten a steady job, being a college graduate), Tom and Charlie stop by Sally's apartment, but Sally, an aspiring singer, is busy entertaining a record producer named Allen Green. She calls Tom and Charlie "tiresome" and sends them away.
The next morning, Tom convinces Charlie that Von Sloneker might take advantage of Audrey and they should go to her aid. But when they visit several car rental agencies around the city, they cannot get a car because neither Tom or Charlie can drive or has a valid driver's license. With Fred (who can drive) unable to assist them due to working at his job, Charlie pays for a taxi to Southampton in the outer rim of Long Island. They sneak into Von Sloneker's beach house and find Cynthia and Audrey sunbathing under heat lamps indoors. Von Sloneker insults Audrey and challenges Tom, who pulls a toy gun on him.
Outside, Tom and Audrey walk on the beach. Audrey is pleased when Tom suggests he might visit France, where Audrey will be attending college after the winter break ends on New Years Day. Soon after, in the ironic final shot, Charlie, Tom, and Audrey hitchhike back to Manhattan since they have no car or taxi to take them back to the city.