"The road less traveled never had so many bumps." Jamie Sutherland never expects to connect with her sexy-as-sin neighbor, Joseph Scarbrough, especially after all the failed relationships she's suffered. Not only does she find out he's not quite "the player" she believed him to be, but that his heart bears scars much deeper than her own. Ready to take a chance on this unlikely match, she eagerly awaits their upcoming date and hopes that Joseph is the very companion she's been waiting for all her life. Time and time again, the comical sporadic encounters resume in their loft apartment complex and Joseph eventually reveals that he is the building superintendent in a very unforgettable, Lucky-in-the-Diet-Coke-commercial fashion. While he's proficient in fixing Jamie's clogged sink, he's not all that great at leaving his past behind. When Caroline, his yuppy ex-girlfriend, makes another surprise visit, Jamie's road to something better gets a little rocky. Will Joseph choose the familiar woman with whom he had a history, or the loyal friend who's given him a future?