The next day, on his way to a second doctor's examination, Willie drinks two bromides to calm his pulse. While Willie waits in the examination room, the drug puts him to sleep, and he does not emerge for eight hours. When he finally emerges, the nurse and doctor are apologetic. Willie's pulse is still unusually high, and his back is seriously abnormal, but the doctor sees his earnest desire to be a Navy man and allows him to pass.
Willie returns to Furnald Hall and finds his roommates attempting to master the stripping and reassembly of their rifles. Keefer has previous experience with rifles, and helps Willie and Keggs. Willie accidentally shoots the mainspring out the window, and it gets caught in the gutter. Willie would get a demerit if he was caught outside during study hours, but he would be dismissed if caught with a damaged rifle. He climbs out the window to retrieve the spring, and Keggs climbs out to help. Suddenly, Ensign Acres bursts into the room for inspection. Willie and Keggs nearly fall to their deaths. Willie produces the spring and manages to talk his way out of demerits.
As bilge day approaches, the three roommates study rigorously. Keefer is a natural at "military wisdom," and his devotion to cleanliness catches the eye his superiors and earns him the position of battalion commander. Willie gets a reputation for his mastery of military ordinance, although he just memorizes the manual without understanding it. All three roommates survive bilge day and are finally able to enjoy their first night off. Willie meets May Wynn and takes her out to Luigi's for dinner. To May Wynn's slight displeasure, Willie excuses himself to go visit his parents in Manhasset.
When Willie arrives at his parent's luxurious house, there is a party waiting for him. Willie's father pulls him aside, and they have a conversation about the Navy and life in general. Willie notices for the first time that his father is walking with a cane and has an infected toe. Mr. Keith finds out that Willie has a girlfriend and asks Willie to invite her to the house. Willie heads back to the city. He arrives at the Stork Club very late for his date with May Wynn and finds her sitting with her manager, Marty Rubin. Rubin leaves, but pays for the dinner Willie and May Wynn are about to eat, which offends Willie. May tells Willie that she will fight with him, but not about Robin: "About us."
The couple agrees to go have it out at the Tahiti. There they meet Keefer and his fat, heavily painted girlfriend Tootsie. A spotlight falls on May and Willie, and the MC asks them to do a number as distinguished Tahiti alumni. Willie and May cannot refuse, and they revive the Mozart piece that brought them together. When the song ends, they fight. May says she doesn't want to see Willie any more. He asks why, and to tell him, she asks if he will marry her. He says he can't, and she says that she expected him to say no.
They kiss passionately on the cab ride back to the base, and May softens. She asks Willie if going to college would make her more acceptable in Mrs. Keith's eyes, but Willie says no. May hardens again. When she sees Willie looking at his watch, she explodes, ordering Willie to get out of the car and out of her life. He has no choice but to submit. He says, "I love you," on the way, but May slams the door on his face. Willie humbly accepts twenty demerits for his four minutes of tardiness and falls asleep.
At Sunday's military parade, Willie sees May Wynn in the crowd. She shouts, "I take it all back. You win," and Willie misses his commands and embarrasses himself in front of the entire commandment. Ensign Brain catches him and brings him to the authorities for reprimand. He is eventually handed over to Commander Morton. Morton remembers that Willies got a commendation for his essay on the frictionless bearing, and arranges a compromise. Instead of throwing Willie out of the Navy outright, Morton brings Willie's total to demerit count to forty- eight, two less than the number that requires automatic expulsion. He also confines Willie to the base for the extent of his apprenticeship.
That night, Willy writes a long letter to May, promising to see her as soon as he is free of the base. The next day, Willie's father makes a surprise visit. Willie explains his dilemma, and Mr. Keith reveals that Mrs. Keith has been arranging a more plush duty for him anyway. Willie asks his father to call off his mother. Willie and his father part warmly. Over the next few weeks, Willy avoids all demerits, and elevates himself to thirty-first in his class. May Wynn and Mrs. Keith visit from time to time, but the meetings are simply cordial and polite. The day comes for graduation and assignment of orders. Instead of asking for the assignment he wants, Willie writes in preferences he thinks would show off his devotion and bravery. Instead of the Annapolis communication school that he had been hoping for, Willie receives duty aboard the minesweeper/destroyer DMS Caine.
As the stories of Willie's training and his relationship with May Wynn develop, we begin to feel sympathetic toward Willie. Wouk draws an analogy between Willie's step through the door into military service and Alice's step through the looking glass into Wonderland. Willie enters a world where he stands out like a sore thumb, but his best qualities begin to emerge. The Navy tests Willie in ways that reveal his intelligence, integrity, and willpower. In the Navy, Willie must rely on himself, for he cannot rely on his money or education.
Willie's blossoming independence elicits different reactions from the people close to him. It creates tension with his mother, who tries to shelter Willie from reality. She supported him in his irresponsible decision to be a lounge piano player, never forcing Willie to fend for himself. Now, she strongly opposes Willie's Naval career. Behind his back, she attempts to orchestrate a way for Willie to avoid leaving the country by getting him a public relations job. Willie's father, on the other hand, seems to come to a new understanding with his son as Willie matures as an individual. Their conversations are honest and caring, and portray a deep bond between the two that Willie seems to be discovering for the first time. Willie continues to think that his relationship with May Wynn is only a passing one, but moments of true affection begin to emerge. In moments when Willie doesn't have time to think, he reveals a growing love May.
An important theme of The Caine Mutiny begins to surface during Willie's naval training: the conflict between Willie's intelligence and illogical military procedures and regulations. Willie's intelligence rebels against the military's illogical commands. He tells his father, "What I've studied seems to me like a lot of rubbish. The rules, the lingo, strike me as comical I used to think it was preferable to the Army, but I'm sure now they're both the same kind of foolishness." Odd details of military service pepper the novel. Willie is amused, for example, that the elevators are labelled "HOIST." For the most part, Willie's willpower overcomes the protests of his intellect, as evidenced by his mastery of the passage on the frictionless bearing, the existence of which is a physical impossibility. At the same time, the military provides Willie with a feeling of belonging and brotherhood that had been missing from his life. This feeling helps him smooth over offenses to his intellect. The novel is also loaded with images of wealth out of place, such as the diamond on Mrs. Keith's hand that raps on the rough door to military life, and Willie's Princeton clothes in the dingy nightclub. As Willie becomes a more solid part of the Navy, however, these images fade, indicating Willie's integration and feeling of belonging.