Prep begins by introducing us to our narrator, Lee Fiora, a freshman at Ault. Ault, a prestigious boarding school near Boston, is nothing like the home Lee is used to, and the first scene shows us how different Lee's new academic life is from her old one. Lee is prepared to give a presentation about Roman architecture in her ancient history class, and is horrified when Jamie, the boy scheduled to present before her, gives the exact presentation she planned—it turns out that she accidentally prepared for the wrong topic, having signed up to present about Roman athletics. Panicking, Lee runs out of class. While she crosses the school's grand campus, colorful with New England autumn foliage, Lee reflects on what's happening in her house back in Indiana—she assumes that her little brothers are playing outside, for instance. Suddenly, Lee hears a voice call out to her. The voice belongs to Gates Medkowski, a confident senior girl who is also the very first girl ever to be made a prefect at Ault.
Gates comforts Lee, offering her a bandana to wipe her tears, and tells her that everyone feels like an outsider when they first arrive at Ault. In fact, Gates assures Lee, even she felt like she didn't belong at first, especially because like Lee, she didn't come from the East Coast. Gates, it turns out, is from Idaho. Her kindness makes Lee feel a bit better. But soon, a new source of stress emerges in her dorm room. Lee has two roommates, Sin-Jun and Dede. Sin-Jun is even more of an outsider than Lee, because she isn't American and doesn't speak English fluently. Dede is slightly less of an outsider, since she's wealthy and puts a lot of effort into being popular. However, Lee notices that Dede puts an almost painful amount of energy into her social status, possessing none of the ease that their truly popular classmates do. Dede notices that forty dollars have disappeared from her dresser, and accuses Sin-Jun and Lee of stealing from her, which they both deny. Dede reports the theft to Madame Broussard, the French teacher who runs the dorm in which Lee lives. That night, Broussard announces what has happened at a dorm-wide meeting, prompting speculation. A loud junior named Amy Dennaker takes the opportunity to make fun of Broussard, and a freshman named Little Washington mutters under her breath that Amy is crazy. Lee and Little have a short conversation then and there. Little is even more of an outsider that Lee, because she's black, even though Lee has heard that she's rich. However, Lee notes, Little's race sets her at a kind of safe distance from Ault social life, allowing her to do things like live in a single room without judgment. Little agrees with Lee that people at Ault are strange, and their conversation ends with a cliffhanger: Little dares Lee to find out whether "Little" is her real name.
After this scene, Lee answers a question readers have probably been asking themselves—what on earth is she doing in an East Coast boarding school? We find out that she decided to apply to Ault on her own, after researching boarding schools at the library. At her public school back home, Lee was a star student, and she told her parents that she wanted a more academically challenging school. In reality, though, academics weren't the reason for her desire to go to Ault, Instead, she paid particular attention to the pictures in the school's promotional pamphlets. She loved looking at the campus, and, even more so, the students. Lee confesses that she used to imagine wandering campus with a boyfriend, both wearing wool sweaters. Lee's family responded with skepticism, both because they didn't know why she would want to attend and because of the high tuition. However, Lee ended up winning a massive scholarship to the school, unexpectedly setting her down a very different path from her former classmates. Lee's recollections then skip ahead, to her first day at Ault. She remembers that her father dropped her off, and that she was dressed far more formally than her other arriving classmates. Dede's father met Lee's father and assumed incorrectly, on hearing that Lee's family came from Indiana, that Lee's father was a college professor. After this, Lee felt acutely embarrassed and was impatient for her father to leave. After this, Lee feels so out-of-place that she frequently cries in the shower. At the same time, she reflects, Ault isn't so different from the fantasies she created of it based on the school's brochures. The campus is beautiful and the students are accomplished. The only thing that seems wrong is Lee herself.
Skipping back ahead to the present, Lee discovers that the school is holding a drag dance—that is to say, a dance where girls dress in boys' clothes and vice-versa. Lee plans on skipping the dance, since she doesn't feel confident dancing. The next morning at the school's roll-call meeting, the two prefects announce the upcoming dance by dancing in front of the entire school in drag. Along with Gates Medkowski, there is one other prefect, a senior named Henry Thorpe. Everyone in the school, especially the seniors, erupt with cheers and laughter. Lee is quiet but amazed at Gates' confidence and her graceful dancing. After the meeting, she approaches Gates and awkwardly compliments her, and Gates replies with a modest thank-you. Lee realizes that Gates' modesty is a way for her to pretend to be just like everyone else, in spite of her magnetic personality.
That night, Lee's dorm is crowded with boys borrowing bras and purses for the dance. After everyone else has disappeared, Lee sits in the common room alone and reads the school's old yearbooks. The common room stocks yearbooks going back several decades, and though most people ignore them, Lee looks through them whenever she can. Lee tries particularly to find pictures of Gates. This time, she finds a new one: a candid photo of Gates smiling during last year's graduation ceremony. Lee is totally absorbed staring at the picture. Then, getting ready for bed, she runs into Little in the bathroom. Little has also skipped the dance. Lee asks Little whether she knows Gates from playing on the basketball team together, and when Little says yes, Lee insists that Gates seems different from everyone else at the school. Little says that Gates isn't different at all; her family is rich, like everyone else's. In fact, they aren't the humble Idaho farmers Lee imagined, but owners of an enormous corporate farm. Next, Little reveals the origin of her name. She's a twin, and was smaller as a baby. Her sister is called Big, and goes to school back home in Pittsburgh. After Little leaves the bathroom, Lee sees that the sink is full of her short black hairs. This is important, because a popular freshman named Aspeth has been complaining about someone leaving pubic hair in the sinks—meaning that Lee, suddenly, knows that these supposed pubic hairs are actually the hairs from Little's head.
Shortly afterward, in their dorm, Dede points out that something smells strange and fishy. Lee agrees and even points it out to Sin-Jun, though Dede continues to talk about the problem while Lee tries to deescalate the conversation. Lee is sure that the smell isn't coming from her, but nobody can seem to find its source, and it continues to worsen. In the meantime, Lee gets used to life at Ault, even though she feels like an outsider. She develops something of a friendship with Little. One day she sees several seniors looking upset and finds out that they were rejected from Harvard. In fact, she learns, only two in the entire class were admitted to Harvard—and one of them is Gates Medkowski. In the dining hall that night Lee tries to congratulate her role model, but gives up after watching her co-prefect Henry congratulate her. Instead, she goes home and draws an elaborate card for Gates. She intends to leave it at Gates's dorm room the next night on her way to dinner, but when she goes back to her own room to get the card, she discovers Dede rummaging through Sin-Jun's dorm. Lee barely notices at first, but Dede panics, insisting to Lee that she isn't the one who's been stealing. She's so determined to make Lee promise not to report her that she grabs onto her arms and almost hurts her. Lee leaves, but forgets Gates' card entirely. She hides in the common room to avoid Dede, and then creeps out and rereads her card to Gates. The card now seems ridiculous, and Lee throws it away. Afterward, she's so preoccupied and unsure whether to report Dede that she goes to Little's room. She tells Little about her dilemma and asks to sleep in her room, but Little, who is extremely private, refuses.
The next day, still upset and indecisive, Lee spends the day in the school infirmary. She sleeps and wanders the infirmary before coming across a few pamphlets meant for students struggling with various problems, including one titled "Am I Gay?" Lee considers her feelings about Gates and grabs the pamphlet. She tries to imagine kissing Gates and feels simply confused, but stashes the pamphlet in her desk that night. Her attention is occupied by something entirely different when she returns—Dede has found the source of the dorm's smell, and it turns out to be a dried squid belonging to Sin-Jun. Dede once again tries to persuade Lee not to turn her in, and Lee responds sassily, which is satisfying for her since she has been so uncharacteristically meek during her time at Ault. Sin-Jun apologizes for the squid incident. The next day in class, Lee remembers leaving the "Am I Gay?" pamphlet in her desk. She's terrified that someone will find it and spread rumors about her sexuality, especially since the thief might come look in her room. She rushes back to get rid of it, but discovers the actual thief leaving her room just as she enters—and it's not Dede, but Little. Little explains that she only steals from people like Dede and Sin-Jun, who are too rich to be affected, and that she would never steak from Lee, who clearly doesn't come from money.
Curtis Sittenfeld's Prep is set in an extreme environment. Ault is an unusual setting for a number of reasons. For one thing, it's full of incredibly privileged people, most of whom seem to feel entitled to the educational privileges that Lee has worked for. For another, it's entirely self-contained. Lee's life is contained entirely within the campus of Ault, whether she's eating, sleeping, socializing, or in class. At the same time, this tiny, completely contained setting provides a microcosmic glance at larger social problems, including class and race.
Lee is an obvious outsider at Ault, and only partly because she comes from the Midwest—as we find out, Gates is from a rural state too, but her wealth and charisma elevate her to the top of the school's social pyramid. The real thing that sets Lee apart is her class background. She lacks the easy, secure feeling of entitlement that so many of her classmates seem to have without even realizing it. The worst part of this, for Lee, is that her outsider status makes her self-conscious, which causes her to suppress her naturally outgoing personality. This newfound awkwardness makes Lee feel even more like an outcast, creating a feedback loop that's difficult for her to escape from.
In this first chapter, we encounter the various other outcasts and outsiders of Ault, all of whom exist in contrast to Gates Medkowski. Even the more popular freshmen seem a bit like they don't belong, since they all seem so determined to be popular, and since they seem to use aggression in order to mask their insecurities. Gates, however, is extremely kind and likable, as if she feels so comfortable in her surroundings that she doesn't need to compete with anyone else. Little Washington, meanwhile, is even more of an outsider than Lee, because of her race. As Lee notes, the extremeness of her difference actually seems liberating—her blackness seems somehow to elevate her above the complex social expectations of the school. However, this observation may also reveal a blind spot of Lee's: she doesn't consider that this extreme exclusion might be upsetting rather than liberating, especially when we discover that her white classmates have made the minor but hurtful mistake of complaining about her hair in the sink, mistaking it for pubic hair because of its curliness. Little, for her part, projects so much bravado that she seems nearly invulnerable until Lee discovers her thefts.
Another character who fits in even less than Lee is Sin-Jun. In her case, the factor that differentiates her from others is not class, but nationality. Sin-Jun is Korean, and so she comes not just from outside of the rarified world of wealth that Ault students tend to be from, but from out of the country entirely. She speaks English well, but imperfectly, and this means that she, like Lee, is unable to show her personality fully. While Lee's self-consciousness makes her unable to act natural around others, Sin-Jun literally cannot act naturally at Ault, since she lacks the ability to fully express herself in an English-speaking context. Like Little, Sin-Jun is so clearly different from other students that she lacks both the ability and the pressure to assimilate into the school's social life. This can appear refreshing at times—Lee might be able to blend in if she tried very hard, which actually makes it easier for her to blame herself when she doesn't fit in. However, Sin-Jun, like Little, can experience exclusion that seems truly terrible. The best example of this in the first chapter is her squid snack, which is deemed disgusting by Dede.
Dede herself, though, seems scarcely happier at Ault than Lee, Little, or Sin-Jun. She comes from a wealthy background and tries her best to look like the most popular girls at the school, but she's not quite as fabulously wealthy as many others, and she simply isn't pretty enough to be truly popular. Moreover—as Lee will explain slightly later—Dede is Jewish, a fact that she can't hide because of her Jewish-sounding last name and her appearance. Like Lee, Dede reacts to her feelings of exclusion with extreme self-consciousness. Her self-consciousness causes her to act in entirely the opposite way, though. While Lee tries to hide away and rarely speaks or makes herself noticeable, Dede tries as hard as she can to become popular by running after the most exclusive crew in the ninth grade. Therefore, Dede and Lee seem to have more in common than either realizes at the beginning. Both girls are unable to reveal their true personalities, and Dede, like Lee, seems to live under a nearly unbearable amount of pressure at Ault.
One of the most complex themes Sittenfeld explores here is fantasy. Lee, we learn, once took refuge in the beautifully designed promotional materials for Ault. She felt ownership over the school's campus and over the students whose pictures appeared on these brochures. Now that she actually finds herself living in her fantasy, ironically, Lee is unhappy. What's most interesting about this is that Lee's disappointment doesn't come from boarding school being less magical than she expected. Instead, Ault is as beautiful as it appeared in photographs, and its students seem as intelligent and good-looking as they did in Lee's imagination. The problem for Lee is that she herself ruins the harmonious picture. This is, in some ways, far more difficult than dealing with disappointment about the school. Now, Lee is forced to confront her sadness about disliking Ault, alongside her own feelings of failure.