Why won't Happy go out West with Biff, and why won't Biff stay? Why doesn't either of them get married and settle down?

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When Biff suggests that Happy leave home and head out West with him, Happy initially seems interested but declines the offer. Happy seeks gratification from others and would rather become a success at home, where his bosses and colleagues can witness his accomplishments. He tells Biff,

I gotta show some...

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When Biff suggests that Happy leave home and head out West with him, Happy initially seems interested but declines the offer. Happy seeks gratification from others and would rather become a success at home, where his bosses and colleagues can witness his accomplishments. He tells Biff,

I gotta show some of those pompous, self-important executives over there that Hap Loman can make the grade. I want to walk into the store the way he walks in. Then I’ll go with you, Biff.

In contrast, Biff refuses to stay home because he cannot stand his father, Willy. Ever since Biff discovered Willy having an affair, he has lost all respect for him. Biff also cannot live up to Willy's expectations, and being under the same roof as him is a constant reminder of his personal failures.

Biff and Happy avoid getting married and settling down for a variety of reasons. Happy is a selfish womanizer; he enjoys living a promiscuous life. He brags to Biff about sleeping with different executives' wives and is a notorious adulterer. He also harbors fantasies of becoming a success in business and does not want married life to interfere with his dreams. Although Biff is thirty-four years old, he is still searching for a steady career while trying to chase the American Dream. Biff's relationship issues stem from his father's marital problems, and he also struggles to be with just one woman, like Happy. Overall, Biff and Happy are too selfish and insecure to meet responsible women, get married, and settle down.

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Biff won't settle down because he's still traumatized over finding out that his father was having an affair with a secretary. This also explains why he's not prepared to stay; he's reached the point where he can't stand to be under the same roof as Willy.

Happy won't go out West because he hasn't yet achieved anything in life. Deep down, despite his outward confidence, he's not sure if he'll be a success out West. The last thing he wants is to have to return home to his family with his tail between his legs, not having staked his claim in the world as he and Willy had hoped.

As for not settling down, Happy is too much of a womanizer for that. There's a certain immaturity about his attitude toward women that makes it nigh impossible for him to settle down in a long-term relationship. Happy has internalized Willy's philosophy that all you need to be a success in life is to be a well-liked man. Among other things, this means that, so long as he continues to attract the attention of women, he'll be more than happy to return their interest.

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The answers to both questions lie in the complicated relationships between sons and father. Happy, as the younger son, has grown up in Biff's shadow. He feels a deep-seated need to prove himself to his father. Hence, he won't go west until he can achieve his father's approval. Biff can't stay because he has no respect for Willy. Ever since he discovered his father's affair years ago, Biff harbors a hatred and disgust for his father which often erupts in anger. It also leaves him unable to be satisfied in any job or location for very long: thus, his restless wandering.

The second question is a bit more difficult to answer, but falls under the same reasons as the first. While we can't really answer why someone doesn't get married (I mean, it's not like one can walk up to a stranger and marry instantly), we can trace the problems in Biff and Happy's relationships. Happy is a notorious adulterer and womanizer. Biff never mentions a girlfriend, and seems uncomfortable with the idea. Both of these problems trace back to Willy's relationship with Linda. The sons have seen their mother bullied, emotionally abused, and ignored their entire lives. Biff also knows his father has cheated on his mother. So there's definitely unresolved issues in dealing with their parents' relationship. This is the most likely reason that Happy and Biff cannot "settle down".

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