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When the boys were younger Willy placed many of his dreams into his son Biff. He looked at Biff's athletic abilities and probably lived his dreams through Biff's accomplishments. He was on the road often as a salesman but went his sporting events when he could.
Willy's relationship with Happy was very different. Happy was often overlooked. He loved his father and would do anything to seek out his approval and attention such as bringing it to his attention that he had lost some weight. He continues to seek his father's approval even as an adult.
Willy's relationship with Biff is crushed once Biff catches his father in the hotel room with a female that is not his mother. He sees that Willy has given her the stockings intended for his mother. This sets Biff back emotionally and places a wedge between his relationship with his father.