Three Days in Montego Bay

Three Days in Montego Bay is a story about the frailty of love, its ability to enhance a life, and its inevitable ability to change the destiny of its character’s lives. This story is a nautical romance that begins in the azure waters of Jamaica. Tom, a post-marital philanderer, idles into calm waters of Montego Bay after a self-imposed hiatus from love as he explores many of the world’s historic ports while studiously avoiding the exploration of his own psyche. Anne, who is in Montego Bay with her fiancé, ventures into the same bar in which Tom is whiling away the better part another lost weekend. While she waits for her husband-to-be, Anne recognizes Tom from a few mutual hospital parties with his ex-wife and they strike up a conversation while they wait for Anne’s fiancé to arrive.
Tom, whose only current friend is his yellow lab Dumpster, admits his culpability for his marriage’s demise and while he normally heads to shore to re-stock on booze, food and, uh, companionship, he recognizes, through his conversation with Anne, that his life has merely be a sprint from responsibilities. Money is not an issue for Tom, due to an inheritance from his father, so responsibility is not something forced upon him by the routines of most humans. Anne’s brash fiancé William, Bill to his friends, arrives and announces his need another couple of days to explore the Jamaican coffee business. Anne confides that Tom and she knew each other through Tom’s wife, Donna leading William/Bill to magnanimously volunteer Tom to show Anne around.
Tom and Anne spend three days meandering around the waterfront exploring the Caribbean sites and each other’s background and somewhere along the line, Tom realizes that he has somehow, despite all effort to the contrary, fallen in love with Anne. Tom’s resolve to live a more altruistic love life is put to the test. They part ways before either does something they cross any physical boundaries but that really only adds to longing he feels for Anne. And, we discover later, she has deep feelings for Tom.
Their paths cross again in Chicago where Tom is now a land-locked author and although Anne pretends that it is a chance meeting, she has patterned her new fiancé-free life around her memories of her time in Montego Bay. Anne lives on a boat in a marina near the hustle and bustle of The Windy City where she now works in the financial district as a financial Vice President. Tom has managed to scrape out some normalcy in his life and is forced into a conundrum when Anne invites him out on her boat, even though Tom is getting married within four months.
Any thoughts of a renewed romance are sidelined as Tom and she are attacked by a group of armed assailants while moored near an Illinois park. They escape but not without a severe injury to Tom and the emotional cloud caused by the death of two of the would-be assailants. Tom’s fiancé, Jennifer, arrives at the hospital and tells Tom that she needs some time away from him, indicating that is likely a permanent situation.
Tom escapes to Hawaii to re-evaluate life, love and the hazard of combining the two. Although he appears to be immersing himself, again, in self-loathing, he is actually beginning to identify what makes Tom tick. He has a very good friend Doug who, unlike Dumpster, can voice a constructive criticism when needed. Jennifer arrives to let Tom know that she, too, has done some soul-searching and would be willing to re-explore the idea of a relationship.
Tom’s decision, of course, is the age-old dilemma…how to be both pragmatic, yet romantically true to one’s heart. He broods over how to apply that to a relationship on a trip with Doug and he broaches the idea of love and the life of Tom. Is it possible? Does he choose t