When Randy's mother marries a guy much younger than her he gets worried. When they go to some kind of couples retreat, he asks Monk and Sharona to go and keep an eye on her. So to go in they pretend to be married.
The man charged with murdering Steve's former girlfriend is set free when the only witness against him is shot in the courtroom before he can testify. Mark suspects that his new, rude neighbor murdered his live-in girlfriend.
Karen Stottlemeyer films a documentary of Captain Stottlemeyer's division. Despite the Commissioner's objections, Monk helps solve the case of a headless corpse, a fatal fire at a wig factory, and a hat thief all in one fell swoop.
A mob boss needs Monk's help to figure out who murdered some members of the family. Monk reluctantly takes the case when the FBI offers to help get him reinstated in exchange for the information he gathers.
Sharona takes a break from Monk so that she can concentrate on her creative writing class, but gets caught up in a twisted murder plot that causes her to question her sanity. Meanwhile, Monk is distracted by Sharona's replacement, who is determined to fix him.
When organic farmer Sarah meets a man who claims to be from 1787 named Rip Van Winkle Jr., she soon discovers old fashioned romantic feelings that might be just as crazy as his story. Starring Torrey DeVitto, Niall Matter.