Cool knows his ultimate destiny is to become a published author. It’s just that the publishers who reject his work don't yet know it. So he first tries his hand at teaching writing, and that’s when his problems begin.
His best student, Gypsy, develops a serious crush on Cool. A transfer student from Scandinavia and a by-product of a broken home and an abusive father, Cool tries to offer Gypsy some adult supervision in her life that seems to be missing. Instead, he wanders off course down that slippery slope of the teacher-student love affair that he knows could get him fired.
After confiding his dilemma to a fellow teaching colleague named, Sierra, she advises Cool to break things off with Gypsy immediately. In the process of trying to help out Cool, instead Sierra falls madly in love with him herself and sets off a competition with Gypsy in a vicious love triangle.
As the relationships between the three of them rise to a crescendo, Cool is forced to make a choice. So, Cool announces his resignation from teaching to run off to Europe and write the great American novel, enrolling Gypsy in college and inviting Sierra to join him on his personal journey. Sierra loves a man willing to risk everything to chase his dream.
Cool and Sierra discover an abandoned farm villa in Portugal where they become “squatters.” Cool finishes a novel and makes the acquaintance of Hillary Shark, an independent publisher. The moment she finishes reading his manuscript she offers Cool a book contract and invites him to London to join her on an extensive book tour to promote his first novel. Of course, the relationship between writer and publisher quickly becomes compromised and complicated, setting off a new love triangle with Sierra waiting in the wings for Cool to regain his senses.
In the end, the book is about the fickleness of fame and fortune. Waiting in the shadows for Cool is the dark underbelly of the publishing industry ready to crush him. That is until Cool finally discovers the perfect poison pill to fight back with and regain his freedom.
