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.