In their initial exchange in Fitzgerald's "Winter Dreams," Dexter encounters both Judy and her nurse. The nurse refers to Dexter in a subservient manner, almost as if he is a servant: "Miss Jones is to have a little caddy, and this one says he can't go." When Dexter explains his reason for not being able to go involving responsibility, Judy simply dismisses it for her own pleasure:
"Well, he's here now." Miss Jones smiled cheerfully at the caddy-master. Then she dropped her bag and set off at a haughty mince toward the first tee.
These comments and actions help to convince Dexter to simply quit his work at the club as a caddy.
The combination of both what Judy Jones and her nurse say and do triggers a variety of emotions in him. One such emotion is determination. The combination of both the nurse's and Judy's reactions help to create a belief in Dexter that he must take action so that he will never be in such a position again. Dexter uses this determination to both "win" Judy in a tangible sense and to achieve a sense of status and position that will enable him to experience the "best." Dexter's "winter dreams" become forces of determination that compel him to believe that he can be better than what he is and envision a world where status, "glittering things," and Judy Jones all go together.