Resolving the cliffhanger set up at the end of season four, the fifth season of Cheers begins as Sam (Ted Danson) attempts to propose to Diane (Shelley Long) via telephone. Diane is receptive, but insists that Sam repeat his request in more romantic surroundings. Thus it is that Sam rents a boat and pops the question to Diane somewhere on the high seas -- and why Diane ends up walking the plank. With this episode, former recurring actor Kelsey Grammer becomes a regular in the role of Dr. Frasier Crane.

After innumerable turndowns, Diane (Shelley Long) finally accepts Sam's marriage proposal, only to be told that the offer has expired. Unwilling to take no for an answer (though she's proven more than willing to dish it out), Diane vows to break up Sam's romantic weekend with another woman at the Sea Shadows Inn. Unbeknownst to Diane, her rival has not shown, forcing Sam (Ted Danson) to go through an elaborate charade.

Hoping to enrich himself in the process, Cliff (John Ratzenberger) sets up a date between his mother Esther (Frances Sternhagen) and wealthy Duncan Fitzgerald (Richard Erdman). It looks as though Cliff's machinations are going to pay off when Fitzgerald proposes. Alas, the old fellow puts a crimp in Cliff's plans by bequeathing his millions to charity.

Bowing to the positive response garnered by the one-shot guest appearance of Bebe Neuwirth in the third-season episode "Second Time Around," the producers of Cheers hired the actress to repeat her performance as uptight psychologist Lilith Sternin in the fifth-season offering "Abnormal Psychology." Having struck out with Lilith when he took her on a date, Frasier Crane (Kelsey Grammer) is trepidacious when he is asked to debate with Lilith on a TV program. Convinced that the hostility between the two doctors is actually a roundabout declaration of mutual love, Diane (Shelley Long) conspires to play matchmaker between the two warring "shrinks."

Carla (Rhea Perlman) prevails upon Cliff (John Ratzenberger) to find her a nice new house at a low price. This Cliff does, only to discover that Carla's new domicile was built on the site of an old prison graveyard. In the fine tradition of Abbott and Costello, Carla and Cliff endeavor to prove that her house isn't haunted by spending a long, long night in the spooky old place.

Ever in search of the Main Chance, Norm (George Wendt) sets up a new business, a combination tanning salon and laundry. The Cheers gang is so certain that this enterprise will strike gold that they talk the reluctant Norm into allowing them to invest in the place -- only to sing a different tune when the business shows signs of imminent failure. Meanwhile, Diane (Shelley Long) persists in her efforts to win back Sam (Ted Danson).

Hoping to prove to Diane (Shelley Long) that he still has celebrity status in Boston, Sam (Ted Danson) books a reservation at the town's most exclusive restaurant. Diane is duly impressed -- and not a little astonished -- when Sam arranges to "accidentally" bump into Diane and her date at the swanky eatery. What Diane doesn't know is that Sam cut through the restaurant's three-month waiting list by impersonating a famous heart surgeon.

Cliff (John Ratzenberger) wants to nominate Norm (George Wendt) for membership in his lodge, the Knights of the Scimitar, but Norm isn't interested -- especially after being apprised of the lodge's draconian rules. Meanwhile, Sam (Ted Danson) suspects that Diane (Shelley Long) is trying to arouse his jealousy by fabricating a handsome boyfriend. It turns out that Diane's friend does exist -- and he is most decidedly a "boy."

Thanksgiving is approaching, but only Diane (Shelley Long) has made plans to celebrate the holiday (and elaborate plans they are indeed, replete with Pilgrim costumes). So that no one will be left out of the festivities, Carla impulsively invites the Cheers gang to dinner at her place. As they impatiently wait for Norm's turkey to finish cooking, Carla can take heart in the fact that, no matter how disastrous the dinner may turn out, at least Diane won't be showing up -- or will she? Vera, the much talked about, but never seen, wife of Norm Peterson (George Wendt), makes her first on-camera appearance -- sort of.

Forever in a state of denial, Diane (Shelley Long) convinces herself that the rejection letters she keeps receiving in a poetry magazine actually hold out promise that her work will one day be accepted. To prove that those rejections slips are merely form letters, Sam submits a poem to the magazine -- and is immediately published. The outraged Diane is convinced that Sam plagiarized his poem, and moves heaven and earth to verify her suspicions.