In 2001 in New York City three friends, who all showed signs of brilliance in their youth, reach their 30s without having achieved the promise they showed a decade earlier. Danielle Minkoff is the only one of her friends to hold a steady job, working as a producer for a TV program that makes documentaries. Marina Thwaite is the daughter of a revered literary critic and author Murray Thwaite who was offered a book contract to write about children's fashion years earlier and, having used up all her advance money and facing a hard deadline, moves back into her childhood home with her parents. Meanwhile, Julius Clarke who is a brilliant and witty critic for The Village Voice cannot sustain himself with his literary work and is forced to take temp jobs to supplement his income which he finds demeaning. At one of his temp jobs he meets a successful, slightly younger, man called David Cohen and seduces him, eventually moving in with him and allowing himself to be kept like a housewife. He keeps Marina and Danielle away from David.
Meanwhile, Danielle begins two flirtations, one with Ludovic Seeley, an Australian editor who has moved to New York City to start a literary journal called The Monitor , after Le Moniteur Universel and another with Marina's father Murray, who begins an email correspondence at first using her job and later concern over Marina's unemployment as reasons to keep contacting her.
Marina, still hanging on to the last traces of her It-girl status, is unsettled by the arrival of her 19 year old cousin Bootie, who has dropped out of university in order to pursue a program of educating himself by his own design. Bootie reveres the Thwaites and looks up to his uncle Murray in whose footsteps he wants to follow, but Marina is dismissive calling him "Fat Fredrick" and find the fact that he is installed himself in the Thwaite home creepy. Despite this things quickly fall in line for Bootie. Murray is impressed by both his desire to leave his small town and his desire to self-educate. He offers him a salary and work as his private secretary. Through Marina, Bootie also is able to rent Julius' old apartment.
Though Danielle is more attracted to Seeley she makes the mistake of introducing him to Marina as a possible editor for his magazine and watches from the sidelines as the two begin to work together and start a relationship. Seeley also inspires Marina to begin to work on her book anew which she decides to name The Emperor's Children Have No Clothes , inspired by something that Seeley tells her. As the possibility of being with Seeley dissolves Danielle begins sleeping with Murray.
Working as Murray's secretary Bootie discovers that his uncle is not the high-principled man he once thought he was and discovers that he self-plagiarizes articles, blows off low-paying events for star-studded ones and is writing a secret indulgent book called How to Live . Additionally, after discovering Murray's affair with Danielle, Bootie decides to write an exposé on Murray for The Monitor .
Over the 4th of July holiday weekend Seeley and Marina become engaged to the annoyance of Danielle and Murray, both of whom suspect that Seeley has some ulterior motive to take down Murray. Around the same time Marina finishes her book and gives it to Murray to read. Finding it vapid and soulless he urges her not to publish the book causing a rift between father and daughter. Around the same time Bootie finishes his exposé on Murray and gives copies to his mother, Marina and Murray. Expecting them to applaud him for his honesty he is shocked when all three are horrified by what he has written. Making matters worse, Seeley, likes the piece and wants to publish it causing a fight between him and Marina.
Bootie becomes estranged from the Thwaites. Furthermore, after David loses his job, Julius takes back his apartment causing Bootie to move to rent a room in an apartment and begin temping downtown.
Marina goes forward with publishing her book and with marrying Seeley. At their wedding Danielle asks Murray to spend an entire night with her, something he has never done, always returning home after their trysts to his wife Annabel. Murray has a cancellation on September 10 and thus decides to spend that night with Danielle. They spend the evening together and the following morning are able to see the September 11 attacks from Danielle's apartment window. Terrified about what has happened Murray abandons Danielle to go to Annabel. Danielle is heartbroken, realizing that though she thought of Murray as her soulmate he has chosen Annabel over her. At The Monitor headquarters Seeley realizes that the project is completely doomed as the launch was to take place that day but the attacks mean that the magazine cannot go to print and that all the articles seem obsolete anyway. Bootie's mother Judy waits to hear from her son and becomes disconcerted as days pass and she hears nothing. She enlists the Thwaites to help find her son and though they manage to track down the temp agency where he worked, they are unable to locate him and assume he has died.
In a state of shock over her breakup, Danielle contacts her mother who takes her on a vacation to Miami. While there Danielle sees Bootie working as a waiter. She tries to talk to him but he tells her his name is Ulrich New. After she leaves him he goes back to his hotel to flee once more.