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Dexter is desperate to validate his existence through success and status, but he is also critical of his attempts to transcend his humble origins by blindly pursuing wealth and sophistication. Dexter both celebrates and denies his middle-class background, and he himself ultimately becomes the obstacle that stands in the way of the personal happiness he seeks. Dexter is unable to resolve this essential conflict of identity. Having finally achieved guest entrance to the country club, he feels like a trespasser, while at the same time feeling superior to the captains of industry whom he finds boring and lacking in golf skills. This inherent duality in Dexter is evident in his complex history with Judy. Although he is able to convince himself that he does not want her as a partner or wife, he cannot control the ardor her presence in his life triggers.

Dexter deliberately creates obstacles to his own happiness. Afraid of commitment, he prefers a solitary existence, hovering on the edges of a world of carousing and bachelorhood. He once coveted a life of financial ease, but when he finally reaches his goal, he feels like an outsider because he had to work hard for his money. He feels that his newly acquired status has been purchased rather than deserved. The satisfaction he feels at becoming the richest young man in the upper Midwest leads him to pursue unattainable goals, such as the possession of Judy Jones. He is blind to his emotional failings and personal shortcomings, seeing little distinction between the personal and professional. For him, love and money are inextricably linked. Dexter’s fixation on the ideal proves to be the most significant obstacle to his happiness. He persists in believing that Judy is an ideal woman, when in reality she is flawed and human. Her transformation into a homely housewife ultimately shatters Dexter’s illusions and ideals.