During his last few days in New York, Tom grows anxious as he ties up his loose ends. He has no family business to attend to, as his parents drowned in Boston Harbor. As a result of that tragedy, Tom “hates water.” Tom tells his roommate, Bob Delancey, that he’ll be moving, but does not tell him where. He visits his former residence, a house owned by a vain, shady man named Marc Priminger, “to pick up a couple of things,” but does not tell Marc of his plans either. “The only friend he feels like telling” is a woman named Cleo Dobelle, a painter who lives “in her own suite of rooms” in her parents’ home. He tells her about his visit to the Greenleaf shipyard, and his return to the Greenleafs’ apartment for another dinner—at which Herbert “had presented him with a wristwatch.” Tom tells Cleo proudly that Herbert has “adopted him like a son.”
Tom’s hatred of water is not significant enough to deter him from taking the trip, but it’s nonetheless symbolic of his fear of his own past. Tom seems to dislike almost everyone in New York except for Cleo, and he tells only her of the once-in-a-lifetime offer that’s been given to him. He exaggerates not a small amount regarding Hebert’s having “adopted him like a son,” but it’s unclear whether he truly believes this fact or whether he simply wants to impress Cleo.
The following day, Tom picks up several things from Brooks Brothers that he’s been instructed to take to Dickie. He chooses the things that he thinks Dickie will most like, and charges them to the Greenleafs’ account.
Tom is already trying to align himself with Dickie’s thoughts and preferences. He is freely spending the Greenleafs’ money before he’s even left the States.