What do Dexter's dream suggest he wants for the future? Why do you think Dexter is so captivated by Judy Jones? These I just can't seem to answer.
Dexter's "Winter Dreams" seem to focus on his obsession with being rich and embodying the trappings of wealth. Growing up relatively middle class, he understands from an early age that there is "something different" about how the rich are. He gains this insight from being their caddy. His first exposure to Judy helps to reveal this, in terms of being able to possess an understanding that they carry themselves differently. Dexter believes this is because they are rich. His dream of gaining and being able to display his wealth manifests itself in being able to play in a foursome with the same people for whom he used to caddy, or being invited to an exclusive country club. His dream lies in being able to "rub elbows" with those who are wealthy. This might be why he is so captivated by Judy, as she is a part of this world. The way in which she carries herself, interacts with men, and displays an attitude that poor people simply could not display is why he is so entranced by her. It is also the reason why he weeps at the end because she is so far removed from that world at the end of the story.