In the book, Willie meets May in the summer of 1941, right after he graduates from Princeton. It's when he's trying to make it as a piano player, rather than going into academia as his mother wants. May is a new singer at the club that he's hired at.
They date until Willie enters the Navy in late 1942. Willie doesn't tell his mother about her, as he believe his mother would disapprove as May is from a poor family and also Italian-Catholic. (May's real name is Marie Minotti, but she's changed it for her singing career.) He DOES tell his father about May though, while he's at midshipman school. His father says that he thinks that both the Navy and May are having a good effect on Willie, and he'd very much like to meet the girl. (Willie's father dies of a melanoma not long after Willie leaves for the Pacific).
During his shore leave at Yosemite, Willie and May sleep together but Willie still tries to avoid the subject of marriage. During the year under Queeg, he writes to her often but thinks more and more that he'll end the relationship because if he survives the war he wants peace in his life, not a marriage with a struggling singer that his mother would never approve of.
Following the mutiny, Willie is given leave to go home (he lives in Westchester, New York) for a week. The new Captain of the Caine -a Regular Navy troubleshooter sent aboard to restore order and normalcy after Queeg and the mutiny- allows him to go, as it's uncertain when he'll be free to go again. (As Willie is facing charges too.) While there, Willie tells his mother and May (who he'd finally introduced to each other in San Francisco over a year before) about the mutiny and impending court martial. There, he breaks up with May.
After Maryk's acquittal, Willie's case is dropped. He returns to the Caine and is soon elevated to Executive Officer. He finds himself missing May terribly and throws himself into his work to keep his mind occupied. In June of 1945, the Caine is hit by a kamikaze at Okinawa. Seconds before the plane hits, Willie thinks he's about to die and realizes his only regret is not marrying May when he had the chance. Willie organizes the crew, gets the damage under control and effectively saves the ship. That night, he writes a long letter to May asking for forgiveness and if she would marry him.
No answer comes in the ensuing weeks and months. After V-J Day and surrender in Tokyo Bay, Keefer (who had been Captain) is discharged and sent home. Willie is elevated to Captain and brings the Caine to the Bayonne Naval Yard for decommissioning. His mother picks him up and drives him home. He tells her he plans to marry May if she'll have him. His mother points out that Willie never gave her a chance to get to know May. Willie hid her and kept it all secret -i.e. he made May look cheap, so she took May at the face value Willie put on her. Willie realizes that his mother has a point. His mother says that if May takes him back to bring her around the house. She wants to meet her and get to know her properly.
Willie tracks May down at the club she's working at. She says she was moved to tears by his proposal letter but was too badly hurt still to reply. They talk and decide to give it another chance; as now that the war is over, they have time.
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