At the beginning of the short story "Winter Dreams" by F. Scott Fitzgerald , Dexter's views about the American dream are connected with ideals of fame and fortune. When he is still a caddy, he envisions himself as a wealthy and admired man who owns an expensive car...
At the beginning of the short story "Winter Dreams" by F. Scott Fitzgerald, Dexter's views about the American dream are connected with ideals of fame and fortune. When he is still a caddy, he envisions himself as a wealthy and admired man who owns an expensive car and earns admiration by winning golf games and performing fancy dives off the springboard of the club raft.
Eventually he borrows money, starts a laundry business, and becomes rich. He is able to visit golf clubs as a player instead of a caddy in the company of wealthy men whose golf equipment he used to carry. This is Dexter's first vision of the American dream, but it all changes when he meets Judy Jones as an adult. He drives her boat while she uses the surf-board, and then she invites him to dinner. Fitzgerald writes that "her casual whim gave a new direction to his life."
After that meeting with Judy Jones, the American dream for Dexter is no longer fame and fortune. Instead, it is to win Judy. She has many boyfriends and has received proposals multiple times. She meets and discards boyfriends casually, without any regard for the hurt she might be causing them. Still, for Dexter she is the embodiment of the American dream: a beautiful, wealthy, privileged woman who can take her pick from among the men who court her.
Dexter and Judy have an off-and-on affair. He is aware that she is seeing other men at the same time. He asks her to marry him, but shortly after that, she becomes involved with someone else. Dexter's engagement to Irene Scheerer is in the nature of a compromise. He has not forgotten about Judy. Realizing he can most likely never win her, he opts for Irene as a source of reasonable happiness and stability. However, when Judy reappears and proposes to Dexter, he instantly cancels the engagement and goes back to Judy. It still doesn't work out, but Dexter does not regret the interlude. He realizes that "he loved her, and he would love her until the day he was too old for loving."
We see then, that at first Dexter's view of the American dream is acquiring fame and fortune, but later it becomes the winning of Judy Jones.