Though Dexter hails from a quite respectable background, he's still profoundly dissatisfied with life. He doesn't just want to be filthy rich—though that would be a good start—he also craves the kind of social respectability denied him on account of his father's being a mere tradesman.
That's why he feels the need to caddy at an upscale country club. This gives him the opportunity to rub shoulders with the social elite, the kind of people he's previously only ever been able to admire from a distance. But even here Dexter remains frustrated with his lot. Although he may be closer than ever before to the upper crust, physical proximity only serves to highlight the vast social distance that separates him from them. Even though he's a valued caddy at the country club, he's still just a caddy; at no point have the rich patrons ever accepted him as one of their own. And for good measure, they never will.
That explains why Dexter develops such a powerful fixation on Judy Jones. On the face...
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