Jack and his mother move to a dilapidated boardinghouse in West Seattle, where Rosemary is one of three female residents. The other two are Kathy, a simple-looking, timid young woman who is pregnant and unwed, and Marian, the housekeeper. Marian is a large, ogre-like woman who tells Rosemary to discipline Jack more severely. For this reason, Marian and Jack despise one another.
Jack's two best friends in Seattle are Terry Taylor and Terry Silver. Like Jack, both boys are being raised by single mothers. Taylor's father never returned from the ##Korean War# and Silver's parents are divorced. After school, the boys cause trouble, stealing from local stores, crashing stolen bikes, and admiring guns, particularly the Luger, a pistol used by the Nazis in ##World War II# Silver owns a Nazi armband that he swears is authentic, but that is obviously homemade. While wearing the armband, Silver orders Taylor and Jack around and makes prank calls to people in the phone book with Jewish-sounding surnames, whom he screams at in "pig German."
The boys spend all of their time at Silver's apartment. Jack cannot bring them home because Phil, the owner of the boardinghouse, has forbidden him to bring children back with him. Phil is deformed by burns and Jack cannot help but stare at him in awe and disgust. Jack, Silver, and Taylor admire themselves in a vanity mirror and try their best to look cool. Afterwards, they watch the Mickey Mouse Club and make vulgar references to Annette, one of the show's stars. Jack writes letters to Annette in which he lies to impress her. Initially, Jack receives form letters in return, but when he continues to exaggerate his life and love for Annette, he ceases to receive even form mail from her. Jack is bitter and fantasizes about suffering a debilitating accident in front of Annette's house, leaving her no choice but to take pity and care for him.
From the roof of Silver's apartment, the boys spot a man driving a Thunderbird, a car they regard more highly than even a Corvette. They pound the driver and his Thunderbird with eggs. The driver is furious, but does not see the boys on the roof. Since his car has been hit with quite a few eggs, the driver shows no reaction when he is by yet another egg. This infuriates the boys and renders them silent until Silver screams at the driver, calling him "Yid," a hateful term for a Jewish person.
Jack and his mother attend a mock naval battle where they meet two men, named Gil and Judd, who stand nearby sipping bottles of beer. Gil takes a romantic interest in Rosemary and invites her and Jack back to his and Judd's house for lunch. Initially, Rosemary is hesitant to go. Jack does not like either man very much, although he warms to them eventually. The men promise Jack a hamburger for lunch, and he begrudgingly agrees to go along.
Gil and Judd's house is large and beautiful compared to Jack and Rosemary's apartment. The men nearly forget about Jack's lunch, and eventually give him dish of nuts instead of a hamburger. Gil talks to Jack about sports and is overly enthusiastic in hopes of impressing Rosemary. Gil asks Jack what he enjoys and Jack answers by telling him that he likes riding bikes, although he does not have one of his own. This hits on a volatile topic between Jack and his mother. They have discussed this issue before, and although Rosemary would like Jack to own a bike, she has no money to buy him one. Gil continues to react to Jack's every word with a dramatic flourishes, and feigns incredulity at the fact that Jack does not own a bike. Gil promises that he will buy Jack an English Racer, the best bike on the market. Rosemary argues that she cannot accept such a gift, but Gil insists.
Rosemary goes on a date with Gil later that evening. Marian and Kathy fuss over Rosemary before she leaves, teasing Rosemary about her "mystery man." Marian is appalled when Gil does not come to the door to get Rosemary at the start of the date. Jack worries about his mother until she returns home late that night in tears. Jack goes over to Rosemary's bed and comforts her. Later, when Jack asks about the bike, she does not answer him and he does not dare to ask her about the bike again.
Jack's infatuation with Annette goes far beyond a mere boyhood crush. Throughout his adolescence, Jack feels somewhat unloved and ignored, even by his mother. Jack's desperation for love is most apparent when it manifests itself in his imagination. He fantasizes about suffering a near-fatal accident in front of Annette's house, and thinks that if Annette can only see his helplessness, she will take him in, nurture him, and eventually grow to love him, just as he wishes his mother and father would.
It is clear that Rosemary does love her son, but she often puts her own interests before his, as she does in Chapter 2 when she forces Jack to come with her to Judd and Gil's house, even though it is clear that Jack does not want to go. At Judd and Gil's house, Jack is overlooked not only by his mother, but also by Gil, who has promised to serve him lunch but then only gives him a dish of nuts. Throughout the memoir, Jack fears that he hampers his mother simply by existing, and although Rosemary never explicitly tells Jack that he has encumbered her freedom, he cannot help but feel like excess baggage.
The reader gains vital insight into the relationship between Jack and his mother at the close of Chapter 2. When Rosemary returns, crying, from her date with Gil, Jack immediately notices his mother's pain and embraces her, rocking her in his arms like a mother would her infant child. In this situation, and in many others to come, Jack plays the parent to his own mother, and is forced to use more maturity than is normally required of a young adolescent. Clearly, Jack and his mother depend on one another. Jack does attain a certain satisfaction from consoling his mother, admitting that her need for him makes him feel "capable." This feeling of capability makes Jack feel justified and purposeful in his existence.
It should also be noted that, in her state of weakness, Rosemary is submissive to Jack, just as she has been submissive to Gil, Roy, and Jack's father. This seemingly automatic submission to dominating men, rooted in Rosemary's childhood experiences with her abusive father, figures importantly in her later marriage to Dwight.