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At thirty-four, Biff is well-built but somewhat worn and not very self-assured. Happy, two years younger than his brother, is tall and powerfully made. He is a visibly sexual person. Both boys are somewhat lost, Happy because he has never risked defeat. The two brothers discuss their father. Happy thinks that Willy's license will be taken away, and Biff suggests that his father's eyes are going.
Happy thinks that it's funny that they are sleeping at home again, and they discuss Happy's "first time" with a girl named Betsy. Happy says that he was once very bashful with women, but as he became more confident Biff became less so. Biff wonders why his father mocks him so much, but Happy says that he wants Biff to make good. Biff tells Happy that he has had twenty or thirty different types of jobs since he left home before the war, and everything turns out the same. He reminisces about herding cattle in Nebraska and the Dakotas. But he criticizes himself for playing around with horses for twenty-eight dollars a week at his advanced age. Happy says that Biff is a poet and an idealist, but Biff says that he's mixed up and should get married.
When Biff asks Happy if he is content, Happy defiantly says that he is not. He says that he has his own apartment, a car, and plenty of woman, but is still lonely. Biff suggests that Happy come out west with him to buy a ranch. Happy claims that he dreams about ripping off his clothes in the store and boxing with his manager, for he can "outbox, outrun, and outlift anybody in that store," yet he has to take orders from them.
Happy says that the women they went on a date with that night were gorgeous, but he gets disgusted with women: he keeps "knockin' them over" but it doesn't mean anything. Happy says that he wants someone with character, like his mother. Biff says that he thinks he may work for Bill Oliver, whom he worked for earlier in life. Biff worries that Bill will remember that he stole a carton of basketballs, and remembers that he quit because Bill was going to fire him.