His mother would never approve of his relationship with her, and at this point in his life, he still relies heavily on his mother. Willie feels pleasure because this means that he could pursue May for "[ ] maximum fun and minimum entanglement- (22). .
Deep down inside Willie is earnestly disappointed. He knows he needs a girl to love to break away from the heavy bindings with his mother. It is clear that even his father thinks he is too attached to his mother, "[ ]be kind to her if you come back from the war with enough strength to break away from her- (66).
"I wish I might have met this girl of yours. It seems to me that she, or the Navy, or both, are having quite a good effect on you- (64). Willie's father begins to notice Willie starting to get more mature around the time he is dating May and leaving for the Navy. Yet, he is not sure whether it is May or the Navy that is causing the changes in him. What Willie's father is sure of is that Willie's assignment to the USS Caine will finish the job of making him into a man. Mr. Keith thinks that Willie's immaturity is due to him having his own way to long, and that he needs "[ ] some stone walls to batter himself against- (65). He tells Willie, "I strongly suspect you'll find plenty of them [stone walls] there on the Caine. I don't envy you the experience itself, but I do envy you the strengthening you're going to derive from it- (65). .
It is in a letter from his father that Willie reads his fathers opinion of May and the Navy. In this same letter Mr. Keith reveals to Willie that he is dying. "Willie began to sob. He read the last paragraphs though a blur of tears- (66). The last sentence reads, "Be a Man- (66). This letter is the official turning point for Willie. After he reads this letter, he becomes determined to do his best in becoming a man for his father. .
Upon his arrival to the Caine Willie is disappointed by the lack of military discipline on the ship.