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Woody embarks on his new life as City Councilman. Norm embarks on his new life as civil servant as Woody pulled some strings to get him an accounting job at City Hall. And Rebecca and Sam embark on their new relationships... possibly. Don asks Rebecca to marry him. Will her regular "I've got to marry a rich man" impulse makes her say no? And after seeing her win an ACE Cable Award on television, Sam makes the decision to get in touch with Diane. Sam lies to her about how happy he is in his life, and he suspects that she too is lying about how happy her married life is. But only a visit by Diane to Boston may make both realize what they want in life, which specifically for Sam can be summed up by a comment from Norm: "You can never be unfaithful to your one true love". Cheers.

Frasier and Lilith announce that they are moving in together and as the instigators of the relationship, they invite Sam and Diane over as their first dinner guests. Just prior to Sam and Diane's arrival, the new couple analyze their relationship and who manipulated who into doing what, which starts an evening long argument. As Sam and Diane arrive, the evening goes on a roller coaster of emotions, the major downturn initiated by a secret revealed by Diane. Thus Diane becomes the third member embroiled in the emotional battle for the evening. The dip and the apartment main floor powder room play key roles in how those emotions manifest themselves. Frasier believes that he has the ultimate answer to the evening's problems.

Diane thinks that Frasier is masking romantic feelings for his colleague, Dr. Lilith Sternin, so she launches a plan to fan the flames of love. Meanwhile, Norm and Cliff reluctantly join Woody for a fishing trip.

The Gaines family has recruited Sam and crew to provide liquor and bartending services at the wedding, and as we'd expect, everything goes wrong. Woody is randy for Kelly, while the rest of the gang learns Mr. Gaines would gladly have Woody killed if he learned Woody and Kelly had premarital relations; Kelly tears her dress, and it's seamstress Cliff to the rescue; and the minister has a heart attack and dies in the kitchen, leading the gang to try and keep the dead body hidden in the dumbwaiter and to recruit a last-minute replacement, a completely wasted member of the Gaines family who we learn, after the gang sobers him up, that he hates weddings, leading them to re-inebriate him. And outside the kitchen in the courtyard, the family Dobermans attack everyone who tries to walk past.

Diane and Sam are given a bleak prognosis from a noted marriage counselor.

Thanksgiving is approaching and no one has anything to do except Diane, who is among a select few graduate students one of her professors has asked to spend Thanksgiving with his family, celebrating in the pilgrim's tradition. Diane suggests that the rest of the gang spend Thanksgiving together in Carla's new home. Carla agrees to a potluck dinner, with Norm in charge of the humongous turkey. Woody, Cliff and Frasier are solo for the day, but Sam is to bring his date Wendy and Norm is to bring his never seen wife Vera. They all vow to make this Thanksgiving the best ever. But some invited guests end up being no shows, and one uninvited guest makes an appearance. The guest list ends up being the smallest of the problems that ultimately befall this Thanksgiving. Regardless, this Thanksgiving does end up being a memorable one for all involved and in some ways the best ever.

Sumner Sloan, Diane's ex-fiancé and old English professor, tells her that he submitted one of her old unfinished novels to an editor at a publishing house, the editor who sees promise in it and sees the possibility of it being published. Diane hasn't yet finished it, in fact she hasn't written anything since she started working at Cheers. Sam secretly overhears their conversation, and thinks that their impending wedding may be holding Diane back in her writing career, something she's always wanted. Sam and Diane discuss her writing career in relation to their marriage, they both feel that in the immediate future only one of the two will happen. Each has his/her own feeling of what should happen, each being so steadfast in their view to an extreme. Sam's perspective is based on a daydream he has about himself and Diane in old age together, she having forgone her writing career. When push comes to shove, one of the two makes a unilateral decision for the two of them, that person who has the full realization that the decision is forever. Meanwhile, the guys at the bar make a bet on whether the wedding will actually happen.

For Frederick's second birthday, Sam takes him, and by association Frasier and Lilith, to a Nanny G concert, she being a famous children's entertainer. Woody tags along just because he loves Nanny G. Someone else unexpected once loved Nanny G as well. At the theater, Frasier is certain that he knows her from somewhere, and he finally figures out that she is really Nanette Guzman, his first wife about who he has never told Lilith. Frasier and Nanette married and divorced when they were very young - when Frasier was still in medical school - and he hasn't seen or thought about her since then. When Nanny G wanders through the audience, she instantly recognizes him, a fact Frasier, Lilith and the rest of the audience obviously realize when Nanny G passionately kisses Frasier. Lilith is angry, but Frasier and Nanette apologize to her. As an act of good faith, Nanny G offers to perform at Frederick's private birthday party. Lilith reluctantly lets it happen despite the fact that the emotions between Frasier and Nanette were once obviously very strong, and still very well may be. Frasier has to decide if Lilith or Nanny G is more important to him. Lilith and Nanny G may decide that for themselves.

When Sam learns that a conman has taken thousands of dollars from Coach, he turns to Harry "The Hat" to help them get the money back.

It's the annual St. Patrick's Day battle of sales between Cheers and Gary's Olde Towne Tavern. Not only does Cheers lose the battle of the hi-jinx with an unsuspecting Woody taking the brunt of the battle, Cheers also loses the sales bet. Sam has finally had as much as he can take not only with the loss once again to Gary's but performing the most humiliating task he and the guys have had to endure due to the loss. Sam threatens Gary and decides to pull out one of the biggest guns he knows: Harry the Hat. Sam asks Harry to devise and execute the ultimate plan to beat Gary. Harry refuses. Despite Carla's assertion to take matters into her own hands, Sam finally gives up permanently to Gary. When Sam goes over to Gary's to wave the final white flag, he witnesses in horror what he believes is Carla's master plan. But what he witnesses is part of a deal Gary made with Rutherford Cunningham, who Sam knows better by another name.

Rebecca is planning a bachelor auction at the bar to raise money for Children's Hospital. Despite Rebecca's nonchalance toward his participation, Sam ends up being one of the bachelors, as is Woody (who she actually asked). Both Sam and Woody end up regretting it because of who purchases them. Meanwhile, Lilith and Frasier are in pre-wedding mode. Frasier suggests something that is totally off the radar for Lilith, namely a pre-nuptial agreement. Lilith is shocked and hurt by Frasier's request. This act by Frasier could jeopardize the wedding, as is a resulting $2,000 act by Lilith unless Sam can come up with a plan to get the two back together again.

Because of Woody's civic election win, Sam needs another bartender, a job he gives to Carla. To celebrate, Carla whips up a batch of one of her powerhouse drinks for the guys. The day after, everyone has a hangover. What's worse, Carla, who imbibed and got drunk herself, has a sneaking suspicion that she took someone home and slept with him, that person she believes being one of the Cheers regulars. She confides in Sam alone, and after he tells her it wasn't him, she panics and they both ponder who it could have been, with her worse nightmare having it be Cliff. When her bed-mate ultimately reveals himself, Carla and Sam have to decide how best to handle the information. Two other revelations come to light in the aftermath of the drunken spree. And Sam makes an admission of his own to Carla to make her feel better about her own further revelation.

What is... Jeopardy! (1984)? The answer is the show that is coming to Boston for a one-time only appearance and that Cliff has made it on as a Boston-based contestant. Cliff is cocky about his chances of winning. He is even more sure of winning after he sees the Jeopardy! board topics. An incident at game itself makes Cliff question his long held fascination with the game. A subsequent personal meeting later with Alex Trebek at Cheers restores his faith in what he can do for the overall good of mankind... or at least anyone who watches Jeopardy! Meanwhile, Sam's little black book is missing. Apparently the current holder of the book is working his way alphabetically through the book, calling up women and making dates as Sam to meet them at the roller rink, with the women to wear a black leather mini-skirt and French cut panties. The mystery person is currently at the H's and so Sam enlists Rebecca's help to set a trap for the mystery man.

Rebecca has been chosen as one of six Boston businesswomen to get a makeover for Redbook magazine. She's excited by it, but ultimately goes a little overboard with the makeover itself. Meanwhile, Sam has found out that Gary of Gary's Olde Towne Tavern has sold his bar. Sam wants to start a new rivalry with the new owner of Gary's, a guy by the name of Frank Carpaccio, especially since they won't have any history of Cheers' underdog status in the bar wars. Woody, Carla, Norm and Cliff go along with Sam on the continued rivalry. When Carpaccio's retaliatory prank seems to be more than just a prank, Sam learns that Frank Carpaccio is a mob boss, whose nickname is the Angel of Death. Because of Carpaccio's evilness, the police will not provide Sam and Cheers any protection. Sam believes that Gary is still pulling a prank, he wanting to see the Cheers gang humiliated by pandering to a supposed mob boss. So Sam, Woody, Carla, Norm and Cliff go down to Gary's to meet with Carpaccio, who ends up looking like the stereotypical Italian mob boss. Pretending to apologize to Carpaccio and ask for forgiveness, the Cheers gang instead pull the fire alarm, setting off the bar's sprinkler system. Carpaccio vows to kill them all, their families and pets. Later, the FBI, who heard about what the gang did to Carpaccio, want Sam and the gang to testify against Carpaccio. The FBI offers witness protection to the five, which means they have to take off immediately in a bus waiting outside the bar. Does this mean that they will have to leave Cheers and Boston forever? Or is Gary behind this prank as he has been all the other times? Or...?

Sam loans out his good luck charm to a slumping Red Sox pitcher. The pitcher immediately goes on a winning streak, but Sam begins experiencing a series of accidents.

The Cranes are having their apartment redone and have called in renowned designer, Ivan. They've also got Norm doing the prep work and painting. However, Ivan's ideas are all form and no function. On top of that, he's snobbish and dictatorial. So they fire him. Inadvertently, Norm, by just moving a chair in their living room so that he can spackle a wall, causes Lilith and Frasier to gush about the great placement of the chair in its new location. Norm really does show his talent for what he calls color and "where to place the ottoman", and he is hired to design the Crane's apartment, which he wants kept secret from everyone at the bar. The design turns out to be exactly what Lilith and Frasier want. The Cranes recommend Norm to their yuppie friends of friends, Kim and Robert Cooperman, who also want their place redone. Norm's initial meeting with the Coopermans doesn't start off well. It's because, as Frasier tells him, the Coopermans are snobs who expect their designers, to use Frasier's term, to be "stylish" i.e. gay and flamboyantly so. To get the job, Norm pretends to be what the Cooperman's want. What will the Coopermans do if they find out Norm is just a beer guzzling straight guy, especially as they want to do a favor for their gay interior designer? Meanwhile, Rebecca is afraid that she's looking a little fat, which Sam in particular milks for all he can. And Carla and Woody discuss other uses for Cliff's brain.

Diane is still involved with Sam's brother, but she confesses that she is in love with Sam. So she returns to the bar to give him one last chance to admit that he loves her too.

Rebecca's estranged sister, Susan Howe, is in Boston to shoot a commercial. She's an actress specializing in horror movies. She stops by the bar in the off chance that Rebecca might want to see her. Rebecca doesn't. Sam finds out that much of the sisterly discord is from the Susan stealing Rebecca's boyfriends when they were younger. Sam uses this information in his attempt to bed both sisters. He tells Susan that Rebecca and he are an item, after which she agrees to go out with him. He tells Rebecca that Susan is interested in him, to which Rebecca replies that to get back at Susan, Sam should break off their date and Rebecca would go out with him in Susan's place. So Sam postpones his date with Susan to take out Rebecca, with his date with Susan now later in the evening. However Susan can't wait and appears at the same time Sam is supposed to go out with Rebecca. Sam has to try and manage his dates with both sisters without the other finding out.

It was Lilith that walked in on Frasier and Rebecca as they were about to make love for the first time. All three are shocked at their situation and Lilith, the most confused, runs off to Cheers to get some answers from Sam as to what's been going on with her husband. Sam and the gang at the bar are as equally shocked by Lilith's news as Lilith was to see it. However it's not quite as simple for Frasier, who refuses to take Lilith back as easily as she wants. There is still the issue of the Dear John letter she wrote him. Apparently the letter was written by Dr. Pascal in an attempt to solidify his relationship with Lilith. Dr. Pascal thinks that he will have some say in what happens between himself and Lilith and between Frasier and Lilith. And as the fourth party, Rebecca will also have a say in what happens between herself and Frasier and between Lilith and Frasier.

Sam and Woody make a bet that they can kiss Rebecca before midnight.

Diane gets mad at the guys when she finds out that they took Frasier on a "snipe hunt." But she also doesn't want them to tell Frasier that they played a trick on him.

When City Councilman Kevin Fogarty comes to Cheers on his re-election campaign spouting a whole lot of political nothings that nonetheless woos the crowd, Frasier bets the gang that he can even get a trained monkey on the ballot and garner 10% of the vote. Without a trained monkey in sight, Frasier chooses Woody as a good surrogate. Frasier does indeed get enough signatures to get Woody on the ballot. Woody helps his own political cause when Holly Matheson, a local reporter covering the City Hall beat, mistakes Woody's farm talk as an analogy for the problems of City politics. In an early poll, Woody garners 8% popular support, enough for the gang to concede defeat to Frasier. However, when Fogarty is caught in a public drunkenness spree, the gang figures that Woody can actually win the election and they go full force on his campaign. Frasier takes this task on as his own personal mission, that is until he has a nightmare of Woody as a career politician in the White House inciting a nuclear war. Frasier's pleas to Woody to withdraw from the race may have an unintended effect as Kelly has news of her own.

Cliff goes into the mail order shoe business. At only $19.99 a pop, all the guys in the bar decide to get a pair. When the shoes arrive, the guys are all amazed at how comfortable and good looking the shoes are, but... Meanwhile, Rebecca thinks that she finally has her ticket out of the bar. Daniel T. Collier, the Chairman of the Board of the corporation - which by the way is called Lillian - asks her to organize a cocktail party at his house. Against Rebecca's better judgment, she agrees to hire Sam and Woody to tend bar at the party. The party is going well until Woody empties some garbage into what he thinks is a garbage can, but is really a priceless antique vase. What's worse is that Rebecca accidentally breaks the vase while she's emptying it out. Admissions to Mr. Collier aka Pinky as to who did what to the vase has an unexpected short to medium term result, despite Woody and Sam's best efforts to be the martyrs.

It's Halloween, and the Cranes are arguing about how much of the Halloween tradition, if any, to which they should expose Frederick. Another argument going on, one more traditional, is that between the gang at Cheers and the gang at Gary's Olde Towne Tavern, Halloween a day that bar wars of the prank kind happen. As Sam and the gang decide what to do to Gary and his bar - as Carla states, she wants to be on a winning side of a great scam - Gary already hits. But the pranks come to a screeching halt from Gary's side when he comes into Cheers and announces that he wants a truce as he was just diagnosed with extremely high blood pressure. Sam doesn't believe him and continues to plot. Checking how their own prank on Gary went over, the Cheers gang goes over to Gary's and finds him alone unconscious on the floor. Frasier checks: Gary isn't unconscious, but dead. Seeing Gary on the floor, Sam doesn't believe Gary's dead. After the police and coroner confirm Frasier's check, Sam doesn't believe Gary's dead. When one of Gary's bartenders gives Sam one of Gary's prized possessions, Sam doesn't believe Gary's dead. As Gary's funeral is announced, Sam doesn't believe Gary's dead. After Sam sees Gary inside the casket, Sam doesn't believe Gary's dead. As the casket is lowered into the ground, Sam doesn't believe Gary's dead. Is Gary dead? Regardless, Carla gets her wish.

Sam and Diane agree to find blind dates dates for each other. Diane takes it seriously, but Sam doesn't--assuming that Diane's plan is to set him up with herself. Therefore, he finds a disastrous date for her at the last minute.