While on board the ship, Tom begins to transform himself into the man he pretended to be to Herbert and Emily. He begins by buying a different style of hat and spending more time on deck despite his fear of water. He determines that he will approach this job honestly and give his best effort. He tries to find a copy of the Henry James book that Herbert recommended but cannot. He spends his time on deck in the mornings, and in the afternoons he writes letters to Cleo, the Greenleafs, and even his aunt Dottie.

Dottie raised him after the death of his parents, but he dislikes her intensely, only staying in touch because she has sent him money at times. In the letter, he tells her he is going to Europe but gives no address, thus finally cutting himself off from her, telling himself he will not need her money anymore. He is upset after writing to his aunt and remembers a time when she mocked him to her friends. He reflects on his past four years in New York, working meaningless jobs and petty cons after having come to the city to be an actor.