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.
In a way, Judy Jones is shaped by men who view her as the ideal woman, as they must contort her to fit their fantasy of this vision of feminine beauty and grace. Judy depends on these suitors’ attentions to give her life meaning. Just as Dexter seems out of his element when he becomes part of Judy’s world, Judy too suffers from a kind of displacement. As a child, she adopts the stilted, precocious tone of a daughter of prosperity, and her self-confidence and comportment suggest a maturity beyond her years. Although she is older than Dexter, she addresses him as “Boy,” which reflects not their age difference but different stations in life. When Judy enters adulthood, however, the shallow, immature, and cruel side of her nature becomes clear. Judy’s selfishness, willfulness, and impulse-driven behavior are leftovers from the realm of childhood and belie the polish and sophistication that her adult beauty suggests.
Judy’s lack of humility and inner reserves suggest the negative effects of an overly indulged existence in which she was sheltered from the sting of the real world. Just as Dexter equates professional success with personal validation, Judy sees her radiant beauty as a sign that she deserves great happiness. “I’m more beautiful than anybody else,” she brazenly asserts, “why can’t I be happy?” Judy fails to attain the happiness she seeks because she is unaware of what happiness requires and what path will lead her there. Mired in surface impressions and the flattery that her serial dating provides, she is unable to properly articulate her dissatisfaction. She uses her physical attributes as her sole means of engaging with and interpreting the world. Like Dexter’s, the life she inhabits at the end of the story falls far short of the life she had expected. She is the victim of her malformed impressions of the world and inability to independently discover who she truly is.