After ten days of leave, Willie arrives in San Francisco. He is struck by the beauty of the sun setting over the city, and listens to a record that he and May Wynn recorded of a Mozart aria. Willie comes upon a mysterious letter in his luggage. It is from his father, and came with instructions to open it only when Willie assumed his duties aboard the Caine. Willie writes a warm letter to May, whom he has sworn to forget once at sea. Roland Keefer calls and invites Willie to a party. The party ends up lasting twenty days. Willie revives his lounge singing and wows the military masses with his old hit If You Knew What the Gnu Knew and his ability to easily incorporate names and contemporary references into songs. Keefer makes the acquaintance of an officer in the transportation department and arranges for the roommates to make the trip to Honolulu on a hospital ship. They have a wonderful trip and arrive in Honolulu "arm in arm with two freethinking nurses."
Willie proceeds directly to check on the Caine, while Keefer goes to see about their lodging. Willie learns that the Caine has left without him. Willie tries and fails to find out how to catch up with his ship. He joins Keefer at a party thrown by an Admiral for the nurses. Willie wows the crowd with his musical talent. The admiral is so pleased by Willie's playing that he arranges for Willie to be assigned to his shore group until the Caine returns to Pearl Harbor.
The next day, Willie sees his father's letter again. Having assumed an active duty, Willie decides that he has sufficient grounds to open the letter. What he finds in the letter shocks him. Willie's father is dying of malignant melanoma, which Mr. Keith expects to have killed him by the time Willie reads the letter. The letter speaks frankly about Willie's growing maturity, his love interests, and his military career. Mainly, Mr. Keith stresses that he wants Willie to do his absolute best in whatever he does. Mr. Keith considers himself a failure because he did not challenge himself. He also recommends a study of the Bible to his son. He says all his money will go to Mrs. Keith, save a ten thousand dollar nest egg for Willie. The letter closes with, "Good-by, my son. Be a man."
Willie is deeply affected by the words of his father and immediately sends a telegraph home asking about his health. The reply comes the next day with the expected news of his father's death. Willie tries to act on his father's words, asking to catch up with the Caine, but his request is denied. As most of Europe falls and the battle in the Pacific rages, Willie sits in the Hawaii officer's pool decoding messages.
With time, Willie's grief for his father's death fades and he begins to enjoy life in Hawaii again. Writing to May becomes his chief pleasure, and he often attends the admiral's parties. One morning, Willie is shaken from his sleep by a Mr. Paynter, who introduces himself as an officer of the Caine. The Caine has returned to port, and Willie is to report to the ship immediately. Willie collects his things and departs with Paynter. The Caine is not where it was left, but they finally find her in a repair basin at the base. The ship's hull is dotted with rust spots, chipped paint, and primer, and the deck is coated in tattered magazines. Willie is introduced to the executive office, Lieutenant Gorton. The captain of the Caine, Mr. De Vriess, stumbles in completely naked. After they are introduced, Willie is taken to his berth, which is in the "clip shack," the room on the upper deck where ammunition is stored. There, he meets his new roommate, Ensign Harding.
Willie wanders around the ship and meets his boss, the communications officer Tom Keefer, Roland's brother. The two men get along well, finding a common interest in literature and writing. Keefer is an aspiring novelist. He is the complete opposite of his brother in physical stature, mentality, and culture. Keefer begins explaining Willie's duties, but they are interrupted by the steward's call for lunch.
The death of Mr. Keith father is a shocking event for Willie. Willie feels sad that he had just begun to relate to his father in their final days together, and his father's letter moves him. He is so touched by his father's feeling that he failed in life that he attempts to have his orders reversed immediately in order to catch up with the Caine and do his part in the war. Although Willie cannot transfer immediately, he continues to find inspiration and rededicate himself to the service because of his father's last words. This newfound credo plays a large part in Willie's maturation. Mr. Keith was not a large influence on Willie's upbringing, but his final letter gives him an effective way of helping his son.
It is implied that before Willie departs from New York, he reconciles with May Wynn. May enrolls in college, at least partly for Willie's sake, and the two enjoy Willie's ten days of freedom together before he leaves. Despite their deepening relationship, Willie still plans to break free of May Wynn after he leaves. Even when he does get away, and she is not in front of him, making him feel guilty, he cannot forget her. Immediately upon arrival in San Francisco, he breaks his promise and writes her a letter, internally deciding to postpone the end of their relationship until he is out to sea. Though Willie later fools around with the San Francisco girls and with the nurses on his passage to Hawaii, he also writes to May again, despite his resolve to break off contact. By the time he is engaged in the monotony of the admiral's office pool, the letters he exchanges with May Wynn are his chief form of pleasure. Although Willie is unwilling to admit it, he truly loves May Wynn, and the only barriers to their happiness are his stubborn ego and immature understanding of relationships.
Willie's ship, the Caine, looks like an outdated disgrace of a minesweeper. Being assigned to it, despite his extremely high rank among graduating midshipmen, is a slap in the face to Willie. He cannot understand how he and Keggs, who was ranked more than two hundred spots below him, could have received the same assignment. His ill feelings fester aboard the ship when he meets Tom Keefer, also an educated man, who tells Willie, "This life is slow suicide, unless you read." Willie is further insulted by being assigned to bunk in the clip shack, which is not even a proper sleeping area, and is full of highly explosive materials. The bunks are simply welded to the walls and he is expected to endure the fumes of the boilers and boiling heat of the sun, conditions worse than even those conditions endured by the enlisted non- officers.