So much of people's lives are spent measuring themselves against others. In Part I of "Winter Dreams," Dexter waits in the caddy-shack on the orders of Mr. McKenna who tells him to wait until the caddy master has returned. While he is waiting, a nurse and her ward, an eleven-year-old girl, the daughter of Mr. Mortimer Jones, have come so that the child can play golf. When Dexter refuses to caddy for them because he must attend the shop, and he informs them that there are no other caddies available, Miss Jones and the nurse go outside, where the girl slams her club on the ground with violence and an argument ensues between the child and her nurse.
As soon as the nurse sees the caddy-master she inquires if someone cannot now caddy for them.
"Well?" The caddy-master turned to Dexter. "....Go pick up the young lady's clubs."
"I don't think I'll go out to-day," said Dexter.
"I think I'll quit."
Although "the enormity of the decision frightened him as the thirty dollars a month he earned was not available anywhere else nearby, " Dexter is changed, and he feels he must react:
"...he had received a strong emotional shock, and his perturbation required a violent and immediate outlet."
This is the first of what Fitzgerald calls Dexter's "winter dreams," his dreams of being rich and having the privileges attached to this wealth. Little Judy Jones's actions have given Dexter a new direction in life in the illusions of his youth for which he will later suffer as he has become enamored of her and lets her represent all that he thinks he wants.