In "Winter Dreams," Dexter's being called "boy" in part causes him to stop caddying because he decides that he's too old to caddy any longer. At least, that's what he tells others around him, like his family. However, Dexter has become smitten by Judy Jones, and it is clear that she is of a much higher social class than Dexter is. Dexter is ashamed of his lower-class status, and being called "boy" reminds him that he is just a caddy, expendable in the eyes of the rich men playing golf on the range. He is so overwhelmed by his infatuation with Judy that Dexter decides that the only way to get over it is to resign suddenly from his position as caddy; in other words, a sudden resignation would "cancel out" the sudden infatuation. Dexter's being called "boy" catapults him into his resignation.
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