Looking at the conversation in its entirety, how does Miller convey the boys’ false sense of their success and opportunities?
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Biff and Happy are both trapped in a perpetual adolescence. Both men are tall and well-built, but their emotional development does not mirror their physical appearance. Happy reminisces about his first sexual experience, while Biff handles a football, a sign of his childhood. The setting of the segment, the boys' childhood bedroom, also suggests that they are trapped in their past. Even the names of the two men, Happy and Biff, are childlike nicknames inappropriate for mature adults.
Biff, in particular, is a drifter who demonstrates little sense of maturity or responsibility. He moves from job to job without any particular plan, and is most content working jobs that use his physicality but do not offer any hope for a stable future. Biff is self-destructive, ruining every job opportunity that he might have, and realizes his own failure. He is aware that he is a disappointment and an embarrassment to his father, who holds great aspirations for his son. Biff feels that he is just a boy and must take steps to demonstrate a shift into the maturity of adulthood.
Happy, in contrast, is less self-aware than his brother, yet is equally confused and is similarly immature. Happy has the ostensible characteristics of adulthood including a steady profession, yet his attitude is that of a teenager. He is a manipulative womanizer who manifests little respect for the women he seduces; his euphemism for seduction, "knockin' them over," suggests at best an impersonal connection and at worst a violent subtext. Happy clearly demonstrates aspects of a Madonna-whore complex; he cannot respect women with whom he has sex, believing them to be inauthentic, and instead wishes to have as a partner a person who has "character" such as his mother. This suggests that Happy cannot respect a woman whom he successfully seduces.
Happy's immaturity is perhaps even more apparent in this segment of the play, for his adolescent qualities starkly contrast with his adult lifestyle. Although he has a respectable job, Happy compares himself to his co-workers in terms of physical accomplishment; he believes he should not have to take orders from men over whom he is athletically superior. He thus approaches the workplace with a school-yard mentality, believing that physical strength is more important than intellectual development.
Miller contrasts the ideas that the two men have with regards to success, the major thematic concern of the play. Biff believes himself to be a failure because he does not display the trappings of adulthood, such as a steady occupation and a stable home life, and because he has made mistakes in his life. Happy, in contrast, believes himself to be a failure because although he is ostensibly more successful than his brother, he still feels empty and unfulfilled.