The final chapter of Prep revolves largely around the relationship between Lee and Cross Sugarman, on whom she has had a debilitating crush since her freshman year. This chapter takes place over the course of Lee's senior year at Ault, while she and her classmates begin to plan for their futures and imagine life outside of boarding school. The chapter begins in the middle of the night, in Lee's dormitory. She wakes to see Cross himself standing in her doorway. Lee is otherwise alone, since her roommate, Martha, is visiting Dartmouth as a prospective student. Cross asks Lee whether he can lie down in her bed, and Lee gets the impression, based on his actions and the fact that he smells like beer, that he is slightly drunk. In fact, Lee tells the reader that she associates the smell of beer with glamour and excitement because of Cross. She can hardly believe that Cross Sugarman is lying in her bed. He takes off his shirt, and they have a flirty conversation, arguing about whether Martha tells Lee confidential prefect secrets. Lee remembers that Cross and Martha are together constantly as prefects. Lee makes an insensitive joke about a classmate being a transvestite, and reflects that she has always been too willing to relinquish her values for the purpose of flirting—especially since Cross doesn't even laugh at her joke. He quietly strokes her hair, as he did in the cab back to school on surprise holiday of their freshman year. Cross asks to kiss Lee and she agrees. Their kissing rapidly progresses: Lee realizes that Cross has an erection, and as he tries to lift up her nightgown, he tells her "I want to make you feel good." Lee asks him why, to which he responds "What kind of question is that?" She wonders whether they will have sex, but they stop short of doing so. Cross returns to his dorm in the night. The next morning, Lee is thrilled as she remembers their encounter, but also overwhelmed. She has nobody to discuss it with, since Martha is out of town until the evening, and she feels overwhelmed by the possibility of seeing either Cross or her classmates in daylight. She decides to skip her optional breakfast, and then to skip her required Sunday chapel attendance, which she has never done. She suddenly feels a newfound pressure—whereas before her crush on Cross was so hopeless that she has no ability to affect their relationship, she now feels that any mistake might ruin what they have. That evening, Lee runs into Aspeth Montgomery. Aspeth casually asks whether Cross came to Lee's room the night before. Lee, not offering any information of her own, learns that Cross had drunkenly announced to a group of friends the previous night that he was going to visit Martha to discuss prefect matters. Aspeth assumes based on Lee's confusion that Cross did not visit Martha and Lee's room, and Lee is left to wonder whether Cross intentionally visited her, or merely came looking for Martha, having forgotten she was at Dartmouth.
The next day, Lee attends an important meeting with her college counselor, Mrs. Stanchak. Mrs. Stanchak, she explains, is the counselor given to the lower-achieving students, the ones whose college attendance is considered somewhat less important to the school administration. Lee brings a list of the colleges to which she intends to apply to her meeting, as she is required to. Mrs. Stanchak looks at the list and gently explains that Lee has no safety schools on her list. She is unlikely, for instance, to attend a prestigious school like Brown, both because of her grades and because of the school's high tuition. Lee cries and explains that prestige is only part of the reason she wants to go to Brown. For instance, she argues, she wants to go to a college with interesting people, and is determined not to return to the Midwest. Mrs. Stanchak urges her to research less-selective schools that fit these requirements. The next day, still feeling sensitive and overwhelmed from her interactions with Cross and Mrs. Stanchak, Lee is assigned to wipe down tables in the dining hall as punishment for skipping chapel. When she arrives, Cross is waiting, directing the pre-dinner setup as part of his prefect duties. He nonchalantly tells Lee to leave, assuring her that he will still report her attendance. Lee frets that his dismissal comes from a desire not to be near her, but in their room, Martha reassures Lee that he was merely doing her a kindness, freeing her up from an unpleasant task. Lee asks Martha whether she can picture Cross and Lee as a couple, and Martha bluntly says no—that their relationship will probably remain casual, partly because Cross seems like he wants to remain single. However, she tells Lee not to passively wait, and to be more decisive with Cross. Lee resents Martha's direct, practical approach, feeling that it's unfair for Martha to be senior prefect and have a boyfriend when Lee has none. Martha's boyfriend, Colby, does not go to Ault, and Lee does not envy their relationship, but does envy Martha's luck in general. Over the weekend, Cross comes to Lee's room again in the night. This time, though, Martha is sleeping in the top bunk. While Lee and Cross are in bed, Martha wakes and walks out of the room. Lee is too absorbed to go after her. Lee and Cross, though, do have a short conversation about their own relationship status. She asks him to "act normal" with her in public, and tells him that she doesn't expect him to make romantic gestures like sending her flowers. Lee and Martha speak the next morning. Martha says that she would prefer for Cross not to visit their room at night, especially since all three of them would be punished for breaking visitation rules. Instead, she suggests that Lee and Cross use a spare room down the hall, one occupied by a day student named Hillary on the rare occasion that she spends the night at Ault. They dissolve their tense conversation by joking, and Lee thinks that most best friends might have said "I love you" in that situation. However, Lee explains, she had found girls who said "I love you" to one another irritating and false, and so says only "I'm glad you're not mad at me."
By Cross's third late-night visit, Lee's life feels entirely consumed by thinking about him. She is too busy daydreaming about Cross to even eat normally, although her grades improve, since she is able to focus on schoolwork more easily while she waits for him. The only thing marring their late-night encounters is Lee's own self-consciousness, particularly when it comes to being seen naked. When Cross arrives in Lee's room for the third time, she guides him to the day student room, as Martha had suggested. While they lie together in their new room, Lee feels tempted to tell Cross that she loves him, but knows that this would be considered ridiculous. Soon afterward, the term's long weekend arrives. Lee usually goes home with Martha for the long weekend, but decides to stay at school simply because she associates it with Cross—though she knows that Cross himself will not be staying for the weekend. She thinks about his most recent visit, during which they almost had sex. Lee recalls stopping Cross, partly out of fear and partly because they did not have a condom. Though Cross tried to persuade her, she found herself turning him down, and offering to "do other stuff," saying "I want to make you feel good," as Cross once said to her. She muses that, had Cross responded "Why" in reference to that earlier encounter, their relationship might have been more successful. He does not, though. Lee, determined to compensate for her refusal to have sex, performs oral sex instead. She does not enjoy herself, but does feel a certain solidarity with every other girl who has done the same. Cross compliments her afterwards, which is thrilling for her. Lee happily remembers that occasion during the long weekend, when she is nearly alone on campus, deeply bored and somewhat depressed. She goes to dinner in the dining hall and sees a movie in town with Sin-Jun, wondering all the while what her classmates know about her and Cross. Soon after Cross comes back at the end of the long weekend, they finally have sex, which Lee notes was "inevitable." She remembers Cross gathering wet towels from the bathroom to clean blood off her thighs, and recalls that the water on the towels was hot. She thinks about the fact that Cross must have waited for hot water to come out of the pipes. Lee thinks about the common truism that a person must be happy alone before they can find happiness with someone else. She ruefully disagrees, thinking of her extreme happiness with Cross. Lee even begins going to Cross's basketball games, though she never speaks to him about it. She has played basketball at Ault for years and finds it boring, but in Cross's games she sees a certain raw emotion and shared narrative that she finds compelling, even revelatory—they seem to be the only context in which Lee's peers are open about their feelings. She even sees Cross crying after losing a game, and notices that nobody acts judgmental or awkward about it.
Soon, it's time for Thanksgiving break. As usual, Lee goes to Martha's house in Vermont, where she is always treated with kindness but feels keenly aware that she is merely proximal to wealth, not truly party to it herself. She enjoys herself but is preoccupied with thoughts of Cross. They return to school in time for early college acceptances. Martha is admitted to Dartmouth and Cross to Harvard, but Lee and Cross never discuss college. Cross tells stories of his childhood in New York instead. Cross and Martha, as prefects, have roles as wise men in the school Christmas play before winter break (the other wise man, always an exceptional non-prefect senior, is Darden Pittard). That night, Lee and Cross have sex twice and joke about how Lee once played Christopher Columbus in a play. Lee looks back on this as their "best night," because of the friendly ease of their conversation. After this, it's time to head home for break. Lee usually enjoys her time alone in the airport, but this time, she is invited to join a group of Ault students smoking and talking. The invitation comes from Aspeth Montgomery's roommate Horton, with whom she has no relationship whatsoever. Though none of the students she talks to in the airport mention Cross explicitly, she suspects that Horton's sudden interest is connected to him—after all, though she trusts Cross not to talk about their relationship, she knows that news travels fast at Ault. Once her flight lands in South Bend, Lee wonders, during banal conversation with her parents, whether her mother knows she has had sex. She feels sure that her mother can somehow sense a change in her, and her suspicions are confirmed that night when Mrs. Fiora knocks on Lee's door to ask whether she knows how to use a condom. Lee pretends to be shocked and embarrassed, and her mother more or less plays along. The rest of break passes uneventfully, until her final night in town, when Lee agrees to drive with her father to pick her brother up from a birthday party. Lee's father is cranky on the drive over, and she braces for him to act the same on the way home. However, her father and brother team up on her, teasing her. This teasing is not ill-intentioned and is normal in Lee's family, but it feels personal and upsetting to her in this moment. She wonders whether her unwillingness to let Cross see her naked stems from her family's constant teasing. Lee feels caught in an impossible position. If she is like her family, she thinks, she has betrayed herself, and if she is no longer like her family, then she has betrayed them.
As soon as she returns to school, though, Lee is consumed by thoughts of the yearly Valentine's Day flower exchange. She wonders whether Cross will send her a flower, especially since the exchange is handled by popular girls. These girls, Lee thinks, will certainly keep track of Cross's purchases and possibly even tell other students about them. Martha mentions that she will probably send Cross a flower—though she will send a pink one, symbolizing friendship rather than love—which Lee finds oddly upsetting. She ultimately does decide to send Cross a flower, along with a short, casual note. While Lee is agonizing over the upcoming exchange, she continues meeting with Cross in the day student room. One night, while they are having sex, the fire alarm rings for a drill. Cross rushes out of the room to his own dorm so he will not be caught out at night. Lee feels somewhat resentful about his abrupt departure, in spite of its necessity. While waiting outside with her classmates, Lee realizes later, she had the opportunity to approach Cross, even publicize their relationship, but chose not to. While the students, stuck outside in the cold, desperately wanted the night to end, Lee looks back and thinks about how long ago her Ault days feel—the mundane events, like fire drills, as well as the moments of excitement. Soon afterward, Hillary, the student whose room Lee and Cross go to at night, announces during a dorm meeting that she has discovered a pair of underwear in the room. The other students react playfully to the news, but Lee feels bashful and awkward. Even this does not occupy her for long, though, as her thoughts return to the approach of the flower exchange. Though she has decided ahead of time not to look through her dorm's delivery of flowers at midnight, when they arrive, she wakes in the night and is unable to help herself. She rummages through the basket of flowers that has been delivered to her dorm and finds that she has gotten two flowers—from Martha and from her tutor Aubrey, not from Cross. The next day, Lee learns that Martha has gotten a pink flower from Cross. This means, she realizes, that Cross participated in the exchange and chose not to send her a flower.
Not long after Valentine's Day, Cross hurts his ankle playing basketball and begins using crutches. Lee does not attend the game at which he hurts his ankle, since, in the wake of the flower exchange, she has been distancing herself from Cross somewhat. At dinner, Cross's friend John asks Lee whether she plans on visiting him in his room, making clear that he knows about Lee and Cross's relationship. Dede, who is also present, seems confused—she clearly knows nothing. Lee gets through the awkward moment by conceding that she might "drop by" Cross's dorm. Later, though, Lee is so overwhelmed by the prospect of all that might go wrong that she decides not to visit Cross. She does see him soon afterward, though: he has a minor part in a school production of Hamlet, which he has joined after his injury forced him to give up sports. The starring roles of Hamlet and Ophelia are played by students named Jesse Middlestadt and Melodie Ryan. Days later, Lee hears back from several colleges she's applied to. Rejected from Brown, she opts to attend the University of Michigan. Her desire to go to college on the East Coast, near Cross, is balanced out by a realization that Cross would probably not choose to visit her at college regardless. Lee runs into Cross in a hallway at school and expresses sympathy for his injury, but he brushes her off, then asks her to join him in a nearby empty classroom, where he requests oral sex. Because they are in such a public, well-lit space, Lee is shocked and moved at how comfortable Cross feels being seen naked—she is uncomfortable being seen naked by him, even in the dark. Not long after this, Lee goes home for spring break. Her experience is unremarkable, but she cries as she departs, thinking about how boarding school is a perpetual process of saying farewell to one's family at a young age.
After returning from break, Lee receives a formal note asking her to meet with Mr. Byden, the headmaster. She assumes that the note is related to her meetings with Cross, all of which have taken place after curfew or in forbidden locations. While Lee waits for her meeting with Mr. Byden, she stares at a portrait of Jonas Ault, the school founder. She recalls the story of the school's founding: Ault's daughter had begged him not to depart on a sailing voyage, but he did anyway. When he returned, his daughter had died of scarlet fever, and, wracked with regret, he founded a school in her memory. Lee considers how strange it is that he chose to found al all-boys school in memory of his daughter. Her reverie is interrupted when Mr. Byden explains the reason for their meeting. A reporter from the New York Times will be visiting Ault to interview students, using Ault as a jumping-off point from which to discuss all prep schools in order to analyze the role of these elite institutions in modern life. Mr. Byden explains that he wants the reporter to paint a balanced portrait of the school, focusing on the increased diversity of its once all-white, male, wealthy student body. He asks Lee to agree to an interview, since she can showcase some of the school's virtues. Lee barely thinks about her upcoming interview, though, since she is thinking about Cross. She first fears that Cross will not visit her again after break—and when he finally does, he feels distant and awkward. She understands that their ill-defined relationship has fizzled. Luckily, distraction comes with her interview. The reporter is a young woman named Angela Varizi. Angela explains to Lee that their entire conversation will be recorded, but, when Lee asks her to explain the relevance of some questions—for instance, about the nature of her father's work—she explains that much of the interview will be used for background information. Lee feels uncomfortable when Angela asks her about the school's high tuition, but explains that she is on a scholarship that covers most of the cost. Feeling more comfortable, Lee explains some of Ault's internal language to the reporter—for instance, she tells her about the clique known as the Bank Boys, so-called because their fathers work in finance or because their entitlement means they might as well. She mentions that certain faculty members show favoritism towards them, but denies that this favoritism stems from their wealth or that it is a chronic issue at Ault.
When Angela Varizi notices that Lee is feeling shy, she tells a story about a wealthy roommate of hers at Harvard who carelessly lost a designer coat and then simply bought a new one. Lee, encouraged, shares more: a story about classmates referring to Ms. Moray's wardrobe as "LMC" (lower-middle class), another about girls buying clothes at random, merely in order to wrap contraband vodka bottles in them. Varizi asks Lee questions that she has not considered before—for instance, whether her scholarship status makes her less likely to drink and break other rules. She explains how students can tell which other students are on scholarships: Black and Latino students tend to be, and dorm decor choices can reveal plenty about a person's wealth. Finally, Lee tells a story that she has never told before, about the incident that made her apply to boarding school. She remembers a trip to Florida with her parents, in which they drove through an expensive neighborhood and admired charming old houses with palm trees in front of them. Lee asked her parents why they could not live in such a house, and Lee's father replied, offhandedly, that these houses belonged to people who sent their sons to boarding school. Lee asked only whether they sent their daughters as well. Years later, she believes, that unremarkable conversation made her want to go to boarding school herself. Leaving, she runs into Darden Pittard, who is scheduled to be interviewed next. She tells him that her interview was "weird," then finds Martha. She explains to Martha that the reporter asked her about tuition, which Martha finds strange. Lee notes that the two of them never discuss their different financial backgrounds, and, in fact, that they never explicitly speak about Lee's scholarship.
Later, Martha returns from the weekly school dance—which Lee always skips—with bad news: she's watched Cross flirting with Aspeth Montgomery all night. Soon after, a gossip-oriented section in the student newspaper hints heavily that Cross is involved with Melodie Ryan, one of the stars in the school production of Hamlet. Lee is so upset that Martha tells her to go talk to Cross herself and find out the truth. Lee agrees, but feels self-conscious about possibly interrupting him while he's with Melodie, even while she knows this fear is absurd. Therefore, she decides to wait until after the weekend. This weekend, the newspaper article about Ault is also scheduled to run. Lee looks back on this weekend as an innocent time, regarding herself the way one might regard a naive girl at the beginning of a horror movie. In fact, on Sunday morning, when she goes to the dining hall for breakfast, Lee immediately is confronted by a harsh reality. All of her classmates are bent over the newspaper, and they all regard her coldly—one even tells her not to "piss in (her) own pool." Martha grabs a copy of the paper, and the two of them read. Varizi has published much of what Lee said, though Lee assumed it would be used merely as background information. She describes the "bank boys," speaks about the difference between the dorm decor of rich vs. scholarship students, and, finally, recounts Lee's story of grand houses in Florida inspiring her to apply to Ault. The article's central argument is that Ault and other elite schools, in spite of their efforts to seem diverse, are exclusive and unwelcoming for students like Lee. An unnamed classmate of Lee's is quoted saying that she is not popular. Lee panics and tries to return to her dorm, but Martha, reminding her that they will graduate in a week's time, urges her to stay in the dining hall, stand her ground, and eat breakfast. She realizes that other students will judge her, but, even worse, they will not particularly care—their judgment will be trivial and dispassionate.
In the middle of the night on Sunday, Lee awakens, having gone to sleep before dinner. She decides to visit Cross. When she reaches his room, though, Lee finds only Cross's roommate Devin—one of the bank boys. Devin clearly knows all about their relationship, and makes a few crass comments about it. Before Lee angrily turns to leave, Devin asks her whether she is "fish or cheese." Lee looks blankly at him, and he explains that he needs to know "for the list." He shows her a list of the names of their classmates. Some of the girls' names (though none of the boys') are annotated simply with the word "fish" or "cheese." Frustrated by Lee's confusion, Devin tells her that the words refer to "what you taste like," telling her that every girl fits into one of the two categories. Devin tells Lee that the list is a collaborative project between all of the boys in the grade, but that Cross, the "custodian," has so far refused to fill in Lee's name. When Lee defends Cross, arguing that he may simply be choosing to respect her privacy, Devin laughs. He tells her that she barely knows Cross. Lee storms out of Cross and Devin's room, but hardly sleeps, since her parents call a little after six in the morning. Her mother is sympathetic, and blames the school for allowing Lee to be interviewed. Lee's father, though, is furious. Lee understands that she has broken an unspoken rule—though both she and her father understand that attending Ault was probably a mistake, she never voices this thought out loud. He ends the call by sarcastically apologizing for being unable to afford a grand mansion with a palm tree.
Lee, meanwhile, still hasn't confronted Cross. She looks for him at formal dinner, but Devin tells her that he's gone to the gym to shoot hoops. Lee finds him there. Cross doesn't directly concede that he's been with Melodie Ryan, pointing out that the school newspaper is "written by a bunch of losers," but he doesn't deny the charge either. Lee is determined not to cry—she does not want to be the type of girl who cries in front of her crush, feeling that girls who do so are "ordinary." Determined to provoke Cross, Lee asks him whether she is "fish or cheese." Cross denies being the "custodian" of the list and tells Lee that Devin is "a prick." Cross's patient, calm denials are more upsetting to Lee than anger, since they prove that he simply isn't interested in the conversation. Eventually, Cross asks Lee to tell him why she's come to talk to him. She explains that she doesn't understand his intentions with her—after all, she says, though they had sex, he never spoke to her in public. Cross replies that he never tried to hide their relationship, given that everyone at school was aware of it anyway. In fact, he reminds Lee, it was she who wanted to keep it secret, and she who asked him not to send her flowers—leading him to avoid doing so as part of the Valentine's Day flower exchange. Lee angrily tells Cross that, regardless, he would not have wanted to be her boyfriend. He bitterly replies that he envies her sureness, but, when pressed, admits that she is probably right. When Lee begins to cry, Cross reminds her of how much they both enjoyed their time together. Then they begin to discuss the Times article: Cross tells Lee that her observations were true, and that her mistake was airing complaints in a public forum rather than within the school media system. He also tells her that she is not as unusual as she thinks she is—he assumes that some of her feelings of being an outsider are based on the fact that she spends so much time alone, but reminds her that he spends time alone shooting hoops, and that many of their classmates also spend time alone practicing skills. Lee wonders what skill she has been practicing during her hours of alone time.
Finally, Cross tells her that he, too sometimes feels excluded at Ault, but unlike Lee avoids isolating himself as a result. Devin, he explains, often uses extremely anti-semitic language in his presence. Lee is shocked to learn that Cross is Jewish. He explains that he is Jewish only on his father's side, but, as a result, has the Jewish last name "Sugarman." Lee realizes that she has missed the opportunity to have meaningful conversations with Cross about topics like this. He tells Lee that she might have enjoyed Ault more had she not allowed herself to feel excluded. Lee senses that Cross is going to kiss her, and, suddenly terrified, sarcastically tells him that she will take his observations "under advisement" This sarcasm disrupts their moment of connection, and Lee continues in this vein, asking Cross whether Melodie is "fish or cheese." Cross defends Melodie, and then angrily yells after Lee that she—Lee—is "fish." Lee responds by confessing her long-held insecurity when it comes to boys, and then by telling Cross that he makes her feel worse about herself than anyone else ever has. She is not sure, as she says it, whether this is true. After this, she runs out of the gym. Cross calls her name, but does not follow her. Back in her dorm, she calls Angela Varizi. Varizi assures her that people outside of Ault's community have loved the article. This doesn't help Lee feel better. Angela begins to repeat the story of her roommate's coat, forgetting that she has told it already, and Lee hangs up.
Days later, Lee attends a special dinner for seniors at Ault. She is miserable and only stays at Martha's urging, though she overhears classmates talking about her quotes in the Times article. At the end of dinner, the Ault junior class traditionally sings to the seniors. Just before this happens, Lee's college counselor, Mrs. Stanchak, congratulates her for her bravery. Lee begins to cry while Mrs. Stanchak hugs her. She finds herself gently pulled away and guided away from the gathering. She realizes that the person holding into her is Darden Pittard. He gently reassures her, causing Lee to think that he will be a good father. Darden speaks negatively about Angela, accusing her of having had an agenda—for instance, he says, she wanted to present him as an "angry black guy," though he did not give her the opportunity to do so. Lee wonders aloud why she fell for Angela's agenda, when Darden was able to avoid doing so. He tells her that the difference is her whiteness: black people in white spaces, he says, are used to avoiding drama and conflict, since they are keenly aware that they are subject to additional attention and judgment. They listen to the junior class singing and watch seniors release white balloons into the sky, another Ault tradition. This one, Lee reports from the future, has been discontinued because of pollution. She reflects that the world seems to have changed a great deal since her high school days. Back at Ault, Lee asks Darden whether he had heard rumors of her relationship with Cross. Assuming that Lee wants him to answer in the negative, he assures her that he heard only unsubstantiated rumors. Lee, though, is half-hopeful that he will say yes. Finally, she tells him that she is sorry for the Times article. Hugging her, he responds "I know you are."
A few days later, Martha finds Lee to warn her that the school is recruiting a minority or scholarship student to rebut the Times article, in a speech during chapel. Lee and Martha discuss the article more, and Lee realizes that Martha herself suggested to Mr. Byden that Lee should be interviewed. She feels guilty, realizing that Martha intended this as a favor to Lee. Martha tells Lee that she is well within her rights to express criticism, but that she should expect to deal with the consequences and stand by her statements. Lee remembers Martha's long-ago assertion that Cross would not become Lee's boyfriend. She feels that Martha is somewhat to blame for the trajectory of her relationship with Cross, but does not say so. Martha tells Lee not to let the end of her time at Ault mar her memory of high school. She reminds her of a day on which the two of them rode bikes into town and ate at a diner, telling her to let this memory represent her Ault days instead. Afterward, though, Lee still feels dissatisfied. She goes to find Cross again, imagining that he will be waiting for her and that they will have sex. His room, though, is empty, and Lee realizes that she does not want to be found there for fear of being labeled "psycho." She leaves and announces out loud to herself that nothing more will happen between the two of them. The next morning, in the last all-school chapel of the year, Conchita Maxwell gives the talk rebutting the Times article. Her speech is unoriginal and cliched. Lee hardly listens, and, as she watches her classmates cry nostalgically at the end of chapel, she realizes that they also have hardly listened. The next few days pass in an anticlimactic blur. Lee's family attends graduation and then flies back to South Bend, while Lee tours New England, going to various parties as part of her senior week. At the end of senior week, she hugs Martha and Martha's boyfriend Colby, and then flies home to South Bend.
Finally, Lee tells the reader about what becomes of her classmates. Dede, she says, sends out a funny card shortly after they start college, announcing that she has gotten a nose job. She stays in touch with Dede, who is now a lawyer in New York. In fact, she says, she enjoys Dede's company more after high school and wonders whether she failed to appreciate her sense of humor at the time. Aspeth Montgomery owns an interior design boutique, while Darden has become a lawyer. Martha, meanwhile, is a professor of Classics. Lee explains that, though she was a bridesmaid in Martha's wedding, they now only talk a few times a year. Rufina and Nick Chafee are now married, while Amy Dennaker has become a political commentator. Lee knows Cross' fate, since Martha and her husband once had dinner with Cross and his wife, and since Martha called Cross afterward. Cross works in finance and keeps golf clubs in his car. Lee remembers her college experience, which she did not enjoy at first. Eventually, she says, she moved into an apartment with a girl and two boys, none of whom she knew well before. She recalls the early days of a flirtation or relationship with one of the boys. Telling the girl, Karen, about her feelings for him, she delved into her past, causing Karen to burst out laughing after hearing the name "Cross Sugarman." The world outside of Ault, Lee muses, is far less stressful and less unhappy—and yet, she feels, the anxiety and intensity of her high school days were satisfying in a way that adult life is not. For this reason, the adult Lee finds it difficult to talk about Ault.
After this brief tour of the future, Lee guides us back to her senior year. She describes a party in Boston during senior week, during which she stayed late and slept over. The next morning, boarding the T to go meet Martha, Lee watched crowds of morning commuters, of many ages and races, wearing all kinds of clothes. She remembers feeling amazed that so many people lived full, interesting lives of their own outside of Ault. To this day, she says, that amazement occasionally returns to her.
Even though Lee's relationship with Cross Sugarman ends with an emotional, unpleasant confrontation, she remembers him fondly. In fact, based on the way she describes her feelings as an adult, Cross remains one of the only elements of Lee's Ault experience towards which she feels unambiguously positive. For instance, she mentions that the smell of beer on men's breath reminds her of Cross, even as an adult, and that she therefore enjoys it. One reason for Lee's warm feelings towards Cross may simply be nostalgia: he is her first romantic and sexual partner, and as such, memories of him remind her of exciting moments in her younger years. However, Lee remembers many of her youthful experiences with less fondness, and so we must conclude that her positive feelings about Cross come from another, more substantive source as well. One such possible cause is Cross's insight into Lee's character. Cross is not possessed of extraordinary wisdom by any means. He prefers to avoid conflict, which leads him to keep his criticisms of Ault as vague as possible, and, though he does not intend to hurt Lee or anyone else, he ends up doing so by keeping relationships undefined. However, he does have a certain gift for seeing through Lee's self-delusions. Lee puts a great deal of effort into disguising her vulnerabilities, so she reacts strongly and defensively when Cross manages to pinpoint them. In retrospect, though, she recognizes their final conversation as a truthful one.
The most fundamental and important truth that Cross points out to Lee during their conversation is the fact that Lee's social status is something of a self-fulfilling prophecy. For one thing, he notes, plenty of people spend time alone, and solitude needn't be conflated with isolation or friendlessness. He uses specific examples, including himself, which signals to the reader that he is telling the truth—plenty of Ault students take time for themselves. In Cross's framework, though, solitary time is useful because it gives the solitary person time to practice a skill. This reveals a blind spot of his—like so many people at Ault, Cross places a great deal of value on self-improvement in the realm of measurable, competition-oriented skills. At the same time, his observation contains a deeper insight. Lee wonders, as he speaks, what skill she has supposedly been practicing. The reader might pause at this point and consider what, exactly, Lee has spent her time alone practicing. Much of this time is spent observing others and wondering about their motivations and inner lives. One might conclude that Lee is honing her ability to understand people, or even to tell stories.
Lee also connects with Cross in their final conversation when he reveals that he is Jewish. This moment is complicated, though, by the fact that their relationship already feels unsalvageable. Therefore, Lee experiences his revelation as a bittersweet moment, in which she realizes that they might have had a deeper friendship and discussed more substantial issues. Cross, though, less inclined to be critical of his school, brings up his Jewishness only in the context of a dismissal: he mentions that his roommate's antisemitism does not particularly bother him, or, more precisely, that he does not allow it to bother him. This statement sheds light on a few aspects of Cross's character and Ault's culture. On the one hand, Cross is right, in that Lee has limited her social life at Ault by assuming the worst of both her classmates and herself. She tends to pay great attention to upsetting experiences while ignoring or minimizing moments of inclusion or kindness. Cross, though, does the opposite, and this has an equally deleterious effect. While he enjoys a fuller social life, he also tolerates insulting behavior from his roommate and essentially hides his identity to survive. It seems that the best possible approach is one that both Lee and Cross have ignored. Rather than silently fret over Ault's flaws and resort to self-blame, as Lee does, or become an apologist for the school's worst tendencies, as Cross does, the best situation might simply be to openly and honestly discuss the school's problems. In fact, Cross's claim presents something of a paradox. He argues that Lee might have had more satisfying experiences at school had she been more willing to put aside her complaints and engage uncritically with her peers. However, the few moments of true connection that Lee experiences at Ault are brought about through uncomfortable, honest discussion of the school's problems. She shares truthful moments with Sin-Jun and their friendship becomes stronger, but Sin-Jun does not choose to tell Lee the truth—rather, Lee discovers it, first because of her friend's suicide attempt and then because she inadvertently walks in on her having sex. Lee also shares a meaningful moment with Darden Pittard, prompting her to more fully consider him as a three-dimensional person. Their conversation, though, happens in response to Lee's Times interview, and revolves partially around the issue of race in predominantly white places like Ault. Lee even regards Dede far more positively when they are no longer classmates, partly because Dede is so much more willing to speak candidly about personal experiences, such as her nose job. However, the punishing beauty standards and expectation of staged effortlessness at Ault rule out the possibility of candidness when it comes to such issues. Therefore, while Cross is correct about the need for Lee to remain open to friendship, he ignores the fact that Lee can only like and respect people who honestly confront the problems around them.
Why, after all, are students so reluctant to talk about Ault's culture of exclusivity and homogeneity? To an extent, Sittenfeld hints, they may simply be following a particularly adolescent urge to conform. But Sittenfeld implies that the school administration bears a great deal of responsibility as well. When Lee meets with Mr. Byden in this final chapter, he essentially asks her to represent the school on behalf of lower-income students and to reassure Angela Varizi that Ault is a welcoming environment for people of all backgrounds. Unfortunately, Byden is unwilling to voice these ideas explicitly, because he, like so many other people at the school, is uncomfortable speaking about issues of class or race. Lee notices this discomfort, not once, but almost continuously: she sees that her classmates in Ms. Moray's English class are uncomfortable acknowledging racism at Ault, and she observes that even Martha's family, kind as they are, avoid uncomfortable or impolite topics together. This refusal to discuss charged topics is not limited to wealthy New England families, though—Lee's own family willfully avoids an honest discussion of her emotional life at school, to such an extent that Mr. Fiora becomes angry when she finally speaks about her negative experiences at Ault. In the case of Byden's hedging, though, this unwillingness to confront hard facts backfires. Lee, not fully understanding what is being asked of her, fails to act as the school predicted in her interview. Furthermore, years of repressed anger about her unequal status at Ault lead Lee to speak completely openly with the first person who gives her the opportunity to do so. Cross points out that Lee might have had more success voicing her anger in a school newspaper, and this is not necessarily untrue. After all, Ault students react defensively when outsiders judge their school's culture—for instance, when Ms. Moray criticizes the school's approach to race, students view her as a threat. However, Cross ignores the fact that Ault discourages this kind of self-criticism, making it far harder for students like Lee to feel comfortable sharing their experiences.
Angela Varizi manages to gain access to Lee's thoughts, and even to memories she herself has not considered for a long time, by asking about her experiences in a nonjudgmental way and by listening patiently. She even makes Lee feel less alone by sharing an experience of her own, which she knows will resonate with Lee. For this reason, Lee likes and trusts the reporter. However, readers are likely to have mixed feelings about Varizi. On the one hand, her determination to confront the unpleasant aspects of the book's setting will feel refreshing to many readers, and her article provides a cathartic condemnation of Ault's exclusivity. For Lee, speaking to Angela Varizi is almost therapeutic. On the other hand, some readers will feel that Varizi has taken advantage of Lee, putting her at ease and encouraging her to share personal stories while fully aware of the article's potential to upset or traumatize her. Even while Varizi is arguably doing her job as a journalist, Sittenfeld makes it clear that she is far from the hero of the story. Lee realizes the same thing after desperately dialing the reporter's number, seeking reassurance or comfort. Varizi retells a story that she has already told Lee, revealing that she views Lee simply as a source to whom she can respond with a series of well-worn anecdotes.
To the extent that Lee finds real solace and understanding, it does not come from Varizi, who seeks to understand and condemn Ault. Instead, it comes from people who have no relationship at all to the strange, elite world of boarding school. This does not include Lee's own family. She loves her parents and brothers, just as she loves some members of her Ault class. Still, Lee's family has become entangled in Ault's emotional ecosystem through Lee herself, just as Lee's school friends are entangled in it by virtue of attending the school. Instead, she feels amazed when she watches a range of commuters pass her on the train platform and realizes that they bear no connection at all to Ault. She feels a similar, if less transcendent, thrill when she shares stories of her high school romantic life with a college roommate. The roommate laughs about Cross Sugarman's name, thereby reminding Lee that the world outside of Ault views the school's arcane social hierarchy as absurd and funny. At the same time, Lee does not look back on her school experience in an entirely negative light. She remembers certain people—Martha, Cross, Sin-Jun, Dede—lovingly, and maintains relationships with some. More importantly, she remembers the atmosphere of her high school with nostalgia. The stress and constant conflict of Ault, Lee explains, created for her an intensity that cannot be matched in the adult world. This contradiction means that Lee will forever feel strangely dissatisfied about her school experience. She can neither condemn it nor remember it with total fondness. Lee explains in an early chapter that Ault students love to misuse the phrase "therein lies the paradox." In this final chapter, Lee seeks out Cross, hoping to talk to him and therefore gain some perspective or resolution that will resolve her disjointed feelings about Ault as a whole. She discovers only Cross's roommate, who misuses this very phrase, describing an incident that is not particularly paradoxical. However, the phrase resonates in the context of Lee's emotional life. She wants Cross to resolve the paradox at the heart of her Ault experience—the fact that her happiness and unhappiness stem from the same source, and that the freedom of adulthood by definition will deprive her of the things she loves most about her school life. But she does not find Cross, and is left only with Devin's accidentally keen observation: nothing can be done about her paradox.