Adrian Monk was once a rising star with the San Francisco Police Department, legendary for using unconventional means to solve the department's most baffling cases. But after the tragic (and still unsolved) murder of his wife Trudy, he developed an extreme case of obsessive-compulsive disorder. Now working as a private consultant, Monk continues to investigate cases in the most unconventional ways.

During their travel from Chicago to New York, Harry and Sally debate whether or not sex ruins a friendship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.