The Great Gatsby Questions and Answers
by F. Scott Fitzgerald

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In The Great Gatsby, why did Gatsby's personal dream of rekindling his relationship with Daisy fail even after gaining his wealth?

Gatsby was unable to rekindle his relationship through wealth because he is “new money,” not “old money.” Daisy grew up in old money society and is comfortable in her unhappy marriage because she and her husband understand each other’s way of life. Daisy is uncomfortable with new money people, and would be scared to sacrifice her comfortable world for Gatsby. Gatsby’s inability to achieve his dream through money is symbolic of the unrealistic expectations of the American Dream.

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Gatsby's personal dream of rekindling his relationship with Daisy failed because of their social differences. Daisy is married to Tom, and together they live a rich, comfortable life among elite society. This makes Gatsby believe that all that was necessary to rekindle his relationship with Daisy was money. But it is important to note the differences between old money and new money. Daisy and Tom are old money people, which means that they have been raised in wealthy society and feel they are well-bred and superior to those who were not raised this way. Even though Gatsby is rich, he is not from the same world. Consider what Nick observes about Daisy’s feeling towards the new money society in West Egg:

She was appalled by West Egg ... by its raw vigor that chafed under the old euphemisms and by the too obtrusive fate that herded its inhabitants along a short-cut from nothing to nothing. She saw something awful in the very simplicity she failed to understand.

Here we see that Daisy looks down on people with new money because she cannot grasp their rags to riches lifestyle. Even though her old money society is so close by, it is an entirely different kind of place, with generational wealth and a uniform understanding of social norms. Although Daisy does seem to feel affectionate towards Gatsby, she cannot separate him from his socioeconomic status. He would never fit in in her world, and she is just too comfortable to leave it.

In addition, Fitzgerald uses Gatsby’s inability to achieve his own dream through wealth to comment on and critique the notion of the American Dream. Gatsby believes that all he needs to get the love he is searching for is getting rich. But it is not that simple. He still ends up alone, and, ultimately, dead. His predicament represents how the American Dream that equates wealth to happiness is an unrealistic understanding of reality.

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