Monk goes undercover as an office worker and revels in the office routines and actually starts making friends and a possible romance as he tries to solve a murder that occurred in a parking garage next to the office building as well as who injured the hand of the man who hired him whose hand was slammed into a car door probably by the murderer. But Monk's new found popularity may come to a screeching halt if he won't put on the pair of used bowling shoes for the showdown match between his office team and their rival team.

For the first time in years, Monk has made progress in therapy. But when Natalie discovers that Trudy may be alive, she risks unraveling her boss completely.