How does Jay Gatsby fail to attain his dream?
Most literally, Gatsby fails to attain his dream because he does not win Daisy back. However, it becomes very obvious to the reader over the course of the book that it is not Daisy, the living person, with whom Gatsby is obsessed—it is his idea of her, and what she represents to him in a social sense. Daisy is the embodiment of everything that Gatsby never had.
Daisy represents the wealth, sophistication, and charm that Gatsby always craved and even engaged in criminal activity to attain. The irony that becomes very clear is that the real Daisy falls quite short of Gatsby's standards, being shallow and fickle. This is not readily apparent to Gatsby, however, who sees only the symbolic green light, to the point that it costs him his entire sense of self and eventually his life.
Not only did Gatsby not attain his dream, but he never could have possibly done so in the first place. The dream itself was illusory.
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