Jack Hemingway was a writer his entire life. Growing up on the family farm he began writing short stories that he would make his sisters read. His family's long literary shadow casts dark and daunting across his writing career; filling him with constant self-doubt and uneasiness. Weary of writing books simply to meet contractual obligations, Jack longs to return to the writing of his youth; to write a story that emerges from the heart instead of the wallet. While at a writer's festival in Liverpool, England, Jack meets Carol Moore, the owner of a book shop where Jack purchases a first edition of F. Scott Fitzgerald's, Tender Is The Night. The somewhat smug American author falls for Carole who hasn't the time for his playboy overtures towards her. The vast distance between England and America does not afford their relationship much chance of success. Jack continues his dalliances at home until a crisis of death compels him to choose in which direction his life's journey will head. Unfulfilled emptiness in his personal and literary life or will he forsake the family masculinity for true love and self-identity; and will he be the Hemingway for a new generation?