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Tess goes out with the servers, throws up, and has bad sex with Will. She feels that she has irrevocably changed. She stays up for two nights in a row and returns to work late and hungover. At work, Tess can’t find her expensive server clogs. Will tries to talk to her about leaving without saying goodbye and ignoring him. Tess tells Will that she does not want to mislead him and has been feeling out of control lately. Will tells her that her clogs are probably in the garbage after the yearly clean-out.
Tess gets high and drunk, hugging Will in her drug-induced state. A server, Ariel, drunkenly throws a glass at another server, Vivian, for cheating on her. Tess brings Ariel back to her apartment, kissing her in the cab ride to Tess’s apartment.
Tess is excited for Jake and Simone to return. Tess and Ariel go to a concert and run into Jake there. Jake takes Tess to a diner. Tess asks Jake about his trip home for Thanksgiving, and he tells her that he doesn’t have family and instead goes to Simone’s family home for Thanksgiving. They talk about changing trends in New York City. Jake says he can tell that Tess grew up in a country-club town. He tells her she is a sloppy drunk, and Tess tries to leave. He stops her. She asks why he stopped his doctorate program and accuses older people, like Jake, of resenting her youth because they’ve wasted their own youths and made poor decisions. Jake tells Tess that she isn’t meeting her full potential because she relies on her good looks, adding that he feels an electric pull to her.
Sasha and Tess chat with one of the regulars, Mrs. Neely, who shares stories about her mother’s friendships with writers from the Harlem Renaissance. Tess and Jake run into each other in the restaurant’s cellar. Jake has a bleeding cut on his forearm; Tess licks it. Simone is in the doorway of the cellar and does not say anything. The rest of the night is stressful for everyone at the restaurant. The bottle of wine Tess pulled for Simone ended up being from 1995, not 2002, as the customer had ordered. Simone takes responsibility for the mistake—the bottle she served was the last of its year.
Tess asks Simone why she does not have a boyfriend, and Simone says she is retired from love.
Howard invites Tess to an annual holiday dinner he hosts with Simone for servers who are far from home. It is Tess’s first winter in New York City, and she sees her first snow from the restaurant, which feels symbolic to her.
Tess decides not to go to Howard and Simone’s dinner. She takes herself out for Chinese food instead, admiring the city as a place no one should live in but that she never wants to leave.
Tess buys a new dress for the restaurant’s annual New Year’s Day party. Tess wins “The Person You’d Most Like to be Stuck in an Elevator With,” which flatters her. However, she is shocked by the memory of her real name. She shows her award to Jake, who tells her it’s actually an award for “the biggest whore” in the restaurant. Tess cries and leaves before he can apologize. Simone finds Tess in the bathroom crying and encourages her to forget about her crush on Jake because he is damaged and will hurt her. Tess tearfully admits that she cannot let go of Jake. Tess tells Simone that she dreamed of her as her mother.
Jake approaches Tess and they flirt before hooking up in the back of a taxi.
Tess is bruised from having sex with Jake. She tries to talk to Ariel about it, but Ariel warns Tess that passionate sex doesn’t mean anything without intimacy.
Tess is six months into her first year in New York City. She’s bought a second-hand dresser and is on track to make $60,000 for the year. She parties with the other servers less and meets Jake in a secluded bar. One cold winter day, she sees the homeless man that Will knows in the park. Tess is worried about the man asleep on a park bench in the cold, but she doesn’t do anything to help him. Tess is thrilled when Jake talks about being annoyed with Simone because Tess wants more access to Simone. She asks Jake questions about Simone; he tells her that Simone is 37 years old and that she gave up a full scholarship to Columbia University to help take care of him. Jake treats Tess badly, and she likes it.
Chapter 6 opens with snippets of the server’s conversations. Tess assists a server, Heather, and admires her knowledge of wine. Tess has been studying wine and fine dining.
Despite the gray of the sky and the unrelenting cold, Tess spends happy days with Jake. In her free time, Tess studies the wine atlas and becomes well-versed in grape history. Howard stops her at work to ask if she’s happy at work and what she plans for the next year. Tess knows she has been drinking too much and now buys her own drugs, but she hopes that life carries on as it has. Howard tells her that he and the owner want to promote Tess to server. Other backwaiters have been waiting longer for their chance at this promotion, so Tess will not be popular when it is announced.
Outside Tess’s apartment, a pair of old sneakers strung up in a tree fascinates her. She wonders how long they’ve been there and to whom they belong. She feels anxious wondering if the sneakers will be in that tree forever.
Tess continues to feel that she is losing control of her life because of her restaurant role and party habits, highlighting the theme of Self-Discovery. When she and Jake start hooking up regularly, her life becomes more structured. She studies the wine atlas, reads, spends time with Jake, and works hard at her job. Tess is finding her rhythm. In accepting her loss of control, Tess is discovering what she wants from her life in the moment. This is part of Tess’s coming-of-age arch; she is young and does not have major responsibilities. She gets to live a life devoted to her pleasures, but repeated warnings about getting too involved with Jake and Simone foreshadow that Tess is living too recklessly. While she is happier and her life is more structured, she does not interrogate or reflect on the direction of her life.
Jake is the first one to tell Tess that she is not meeting her full potential, a slow and steady realization that highlights the themes of Self-Discovery and Disillusionment and Experience. Jake’s analysis of Tess—that she leans into her looks and doesn’t use her intelligent mind—is unkind and ironic given their sexual connection. But Tess is like a sponge; she soaks up what other people say and think about her, which emphasizes that she still hasn’t developed her own Self-Discovery. The process of her character development relies heavily on the opinions and interpretations of others, particularly Jake and Simone. While Tess may not be meeting her full potential, she cannot yet comprehend what that potential is. Tess’s world is myopically focused on the restaurant and on modeling herself after Simone. The restaurant makes the enormous city of New York smaller, and Tess primarily operates within that one setting. Thus, the restaurant is both a place of major growth and a place in which potential can be stifled, as could be said for a character like Simone. Moreover, Tess is intelligent, but she does not yet have the tools to combat her sexualization in the workplace. The men at the restaurant want to sleep with her, and despite having a real connection with Jake, he too makes their relationship about sex. As a young woman discovering herself, this sexualized identity interferes with her growth, prompting Tess to focus too heavily on her relationship with Jake and perhaps allowing more sexualization than she is truly comfortable with.
Part 3 is subtitled “Winter.” Winters in New York City are known to be rough—the city gets dirtied by the slush of melting snow, and the continued gray can be weary. Moreover, winter often represents sorrow, death, and a resting period in preparation for the rebirth of spring. For Tess, winter is a time of pleasure because of her new relationship with Jake. So, perhaps, like winter snow or ice, Tess’s life is still and quiet because of her newfound focus in her life. She even improves at work in spite of the melancholy of winter.
When Howard reveals that he plans on promoting Tess, thus bringing her one step closer to becoming more like Simone, it marks a significant plot development and moment of character growth, which highlights both Self-Discovery and The Restaurant Industry and Broader Societal Issues. The promotion is indicative of Tess uncovering her potential and learning her growing role within the restaurant itself.
With regard to romantic Self-Discovery, Tess is happy with Jake, but their relationship is complicated. It is not a defined relationship because Jake remains characteristically aloof. Tess recognizes that Jake often does not seem to realize or care that she is in the same room as him. For Tess, the intense moments of passion with Jake are more important than his emotional distance. Moreover, there is a hint of violence in their sexual connection, indicating Jake’s danger. Tess is so entranced by the experience of passionate sex that she ignores the reality of the situation, thus highlighting the theme of Disillusionment and Experience. Further, the specter of Simone haunts their relationship. Tess is still entranced by Simone and wants to grow closer to both Jake and Simone; she sees a pathway to one through the other. On the one hand, Tess fantasizes about traveling far away with Jake, leaving Simone behind. This implies that Tess is jealous of the history Simone and Jake have together. On the other hand, Tess wants Jake to talk about Simone, implying that she wants to establish intimacy. However, there are many facts about Simone’s past with Jake that are unclear. Tess mistakenly hopes that she can become a trio with Jake and Simone, but it is clear that their shared and mysterious history is more important than Tess realizes.