Fooling the Gatekeepers - Part II

Clued in or clueless?  You decide.
Synopsis provided to literary agent:
The Flipside of Heaven chronicles the life of Justin Loutman from his childhood up through his early twenties. Born the son of a wealthy and sophisticated woman, Alexis, Justin travels the country with his mother until he attends the St. Blaine Academy prep school in a tony North Shore suburb of Chicago. He is handsome, quite intelligent, though lazy in his schoolwork, and, through his mother’s connections, he earns admission to the University of Chicago. Though initially concerned with being a success on campus, after failing a class, he gives himself over to idleness; he prefers to learn through reading and discussions with friends than through his classes. Toward the end of his college career, America is at first shattered, then united by the event of September 11, 2001.  When his country enters into wars in Iraq and Afghanistan, Justin, seized by patriotism, enlists, forgoing his degree. During his tour of duty, Alexis dies. Upon his return to America, Justin meets the young reality show star and minor celebrity, Kendra McClarren, the sister of his college friend, Trip. The two fall in love, but because of the stock market crash and his family's poor investments, Justin has little money, and Kendra does not wish to marry a slacker without the means to contribute support to her chosen life style. Despite Justin's best efforts to earn money at an Internet start-up music-sharing site, Kendra breaks off their engagement in order to marry a wealthier man, devastating Justin. He goes on a three-week coke and alcohol binge, which is finally terminated by his arrest for public indecency.
Justin's quest for self-knowledge begins. He has a short summer romance with the wild Kaitlyn. Soon after, Trip is caught up in a scandal involving the underaged daughter of a Chicago politician, and Justin takes the blame. Justin then discovers that his last close tie, the dear friend of his mother and his father figure, Dr. Gerson, has passed away. Further, the recession and collapse of the Internet start-up have left him almost no money. After attending the funeral in Wisconsin, he decides to hitchhike back to the University of Chicago to try to start again.  As he stumbles through the North Shore he is picked up along the way by the wealthy father of a friend who died in Iraq.  Justin expounds his new socialist principles and then continues to walk to the university. He arrives late at night, pining for Kendra.  Justin reaches his hands to the sky, realizing he knows nothing but himself.
Agent's response:
Thank you for thinking of me with your query for THE FLIPSIDE OF HEAVEN.  While this sounds like a strong project, I'm afraid it doesn't strike me as a likely fit with me and my particular editorial contacts.  I wish you well in finding the right agent for your work.
Reality:  This is essentially a plot summary of F. Scott Fitzgerald's first novel, This Side of Paradise.  
Guess it just doesn't fit that old list.

Well, hey, after all, it's not a paranormal romance! Just a bad one...