The Great Gatsby challenges the reader to understand what Gatsby's motivation was, why he had the fancy parties, whether his means of making money was legal or not and whether his life has meaning and purpose.
Against the backdrop of illegal activities, prohibition, and senseless partying and wild drinking, the author asks the reader to find the depth of the love story that lies hidden in the chaos.
Gatsby and Daisy's lives were disrupted by WW I and then the dawn of an age where everyone seemed to pursue pleasure, without thought of consequence. Fitzgerald is a master at drawing the reader into the Jazz Age, so named by Fitzgerald himself.
Gatsby is a likable guy, he appears to be very generous and has tons of money, he is also a man of great mystery. The reader learns that he has a deep lasting love for Daisy Buchanan, his neighbor in East Egg, a woman he loved and lost due to the fact that he shipped off to war and was not a wealthy man.
The reader comes to care for Gatsby and Daisy's secret love, since Tom, Daisy's husband is such a cruel, indifferent cheater. The sadness that echoes through the book, after Gatsby's hopes are raised and then dashed by the events which unfold, the death of Tom's lover in the car accident, the car that was driven by Daisy.
The reader is drawn in through Gatsby's desire to be so self-sacrificing on behalf of Daisy and her reaction to this is total indifference and escape.
Gatsby is the real victim in this sad story.
Fitzgerald creates a work in The Great Gatsby that forces the reader to perceive meaning in a time period where absurdity was present. The standard depiction of the 1920's, America's Jazz Age, was one of intense pleasure. The mass consumerism that dominated the period led to a sense of indulgence that defined the age. Individuals of this age were taking advantage of cultural media, increased social interaction, and the materialism helped to define reality. Fitzgerald's work is set amidst this backdrop. Through his eyes, we are able to see the hollowness in such a pursuit. We are shown that this monument of culture called the Jazz Age was actually a castle built upon a firmament of sand, and the tide was inevitable. Gatsby's exploits, his pursuit of Daisy, and his emptiness seem to represent much of the age. Throughout the work, Fitzgerald challenges the readers to see past the material trappings, the social notions of the good, and examine the hollowness present. I think you can find many examples of this throughout the work. Within this process, we, as the readers, are compelled to understand meaning in a different way. We see that the characters in the work, seeking to appropriate the world in accordance to their own flawed subjectivity, are, themselves, flawed. Within this fragmentation, there is meaning present. Fitzgerald is imploring anyone reading the work to examine what constitutes social acceptance of the good when this foundation is so empty.