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Harrison Brooks possesses all the qualities most women admire. He's a gentleman first, has made his own wealth and could charm the pants off most girls with his model-quality good looks. He's played hard with the big leagues and enjoyed the likes of many women willing to be his evening's conquest, hoping to capture the heart of the rich playboy. When Harrison meets Monica Green, he leaves his life in Chicago behind to be with her. With trust issues, he allows jealousy to destroy his relationship with Monica, and even more desperate, he magnifies events as an excuse to be a jackass and leave her, shy of the alter. Desperate and drowning in self-pity, Harrison moves back to Chicago and finds his life turned upside down one night at Logan's Bar. The events that unfold help him discover the man buried inside himself that he really wants to become and he finally has a chance at true love. But, will he make more mistakes and find himself in shreds?