Ann Hodges grudgingly agrees to assess Frasier's apartment for a home insurance quote; when she falls and breaks her leg, he decides to take her in and buddy her up, afraid she will sue. Maris is released from jail but kept under house arrest; she draws Niles, Martin, and Daphne into an elaborate scheme to escape the country.
Martin and Ronee's romantic getaway to the country is spoiled when first Frasier, and then Niles and Daphne mistakenly believe they have been invited along. At the cabin, each of them has a nightmare based on their hidden fears: Frasier dreams that he has killed Niles and married Daphne; Niles that he is unable to handle a baby; and Daphne that Niles is cheating on her while she gains weight uncontrollably. Only Martin has a peaceful dream, seeing himself and Ronee at the center of a music hall routine.
Through a series of unnecessarily detailed flashbacks, Frasier confesses to Niles that, bored with his job and jealous of his family's happiness, he has stolen a small trinket from an elderly neighbor's apartment. He and Niles crash her surprise birthday party to try and return it in secret.
Exiting the elevator on the wrong floor of his office building, Frasier runs into Charlotte, a matchmaker looking eagerly for new clients. Frasier declines her help, but changes his mind after a disastrous encounter with an ex-girlfriend. His confidence does not improve when Charlotte sends him on a series of dates from hell. An impressionable Niles and Daphne follow the advice of another couple from their Lamaze class, and hire a midwife who insists on a drug-free birth.
Frasier is taken with Charlotte, but she already has a boyfriend, a ruggedly handsome man named Frank. To try and get his mind off her, Roz takes him to a singles bar, where he meets a sexy and eager young woman named Kim. Martin tries to make a good impression on Ronee's very conservative mother.
Charlotte has to go to a conference and Frasier offers to drive her to the train station. However, they miss the train (numerous times at numerous stations) and end up stranded in the middle of nowhere. They take shelter at the home of an eccentric family, who believe they are married, which causes them to re-assess their relationship. Daphne, Martin and Niles schedule interviews for a nanny, a new physical therapist, and a stripper for Martin's bachelor party, but they confuse which candidate is for which position.
Frasier and Charlotte have one last dinner together before she leaves Seattle for Chicago. Ronnie informs Martin that they booked the wrong date for their wedding, in eight days' time. Frasier and Niles decide that they'll put it all together in time. However, in typical Crane fashion, it's one disaster after another, not the least of which is Eddie eating the rings.