Cheers is a small bar in Boston, MA. As owner Sam Malone opens up, a couple enter the bar. Professor Sumner Sloane and his fiance Diane Chambers are to go to Barbados to be married, but Sumner's ex-wife still has the wedding ring. Sumner asks Sam to keep an eye on Diane for him whilst he goes and fetches it. Sam tries chatting up Diane but she's not interested. The other employees at Cheers arrive for work - waitress and single mom Carla Tortelli, and bartender Ernie "Coach" Pantusso, who was Sam's baseball coach back in the days when Sam was a relief pitcher for the Red Sox. As the bar gets busier and more people wonder who she is, Diane hopes Sumner will return eventually. Sumner comes back a few hours later and says he hasn't got the ring, but then his ex-wife calls and says she's got it, so he once again leaves Diane in Cheers whilst he goes to fetch it. He asks Diane to call the airport and put their flight back a bit. Once again he is gone a long time, and Diane starts to worry t
Frasier has been out on a date with a fellow psychiatrist, Dr Lilith Sternin, but things didn't go too well. Frasier feels depressed, so feeling sorry for him, Sam arranges a date between Frasier and a woman he knows named Candy. But Sam and Diane get a surprise when Frasier proposes to Candy after just one date.
Local councilwoman Janet Eldridge comes to Cheers as part of her re-election campaign, and Sam finds hismelf smitten with her. Janet and Sam become a couple, but a jealous Diane joins the opposition campaign fearing that if Janet wins the election, she will win Sam's heart as well. Meanwhile Frasier also joins the opposition campaign hoping to win Diane back.
Sam and Janet's relationship is getting stronger and stronger whilst Diane gets more jealous. Janet suggests that Sam fire iane to sever all ties with his past, but Diane overhears and quits before he can fire her. Vera's sister Donna is visiting the Petersons and Norm is worried that Donna will flirt with him like she did on her last visit.
Janet has won the election and is hosting her press conference at Cheers. Diane turns up to apologize to Sam but ends up asking Janet some personal questions which causes Sam to throw her out of the bar. Later Sam and Janet talk and realize their relationship won't work, so break it off. Sam then picks up the telephone, rings someone and then asks them to marry him..... Meanwhile Vera has been called away, so Donna is left alone with Norm, much to his horror.
We finally found out who Sam's telephone proposal at the end of the last episode was to - Diane! But Diane fears that Sam is meerely on the rebound after breaking up with Janet, so asks him to repeat the proposal in a more romantic occasion, but when he does (on a boat), she refuses, causing Sam to make her walk the plank. Later Diane says she does want to get married, but Sam has now retracted the proposal.
Frasier and Lilith invite Sam and Diane over for dinner to celebrate their first week of cohabitation. But things start going wrong when Lilith finds out Frasier and Diane were engaged, and she locks herself in the bathroom. Then Sam and Diane have an argument as well. Meanwhile Cliff agrees to babysit Carla's kids.
Jeopardy makes an appearance in Boston, and Cliff gets on the show. The Jeopardy! round had all 6 categories Cliff specializes in, such as celebrities or the US Postal Service. But when Final Jeopardy approaches, he loses all his money putting a stupid response "Who are three people that have never visited my kitchen?" and becomes depressed afterwards. Meanwhile someone has stolen Sam's little black book and started ringing all the girls in it.
A Boston performance by children's singer Nanny Gee for Frederick's birthday sheds light on Frasier's past as Lilith and the barflies discover Nanny is Frasier's first wife! Frasier had forgotten to mention this fact to Lilith and when Nanny arrives at Cheers she and Lilith soon get into a catfight!
Sam ponders a baseball comeback, but when he goes to play a few games he discovers most of the players are much younger and immature than he is. They're acting just like he used to, and Sam doesn't think he enjoys acting like that anymore. Meanwhile, back in Boston, Frasier loses Lilith's favourite lab rat and tries to get an identical one before she returns.
Woody and Kelly's wedding faces some funny obstacles, before and during the ceremony, including Sam's flirtation with a German guest who turns out to be married, the priest dying and Kelly's Uncle Roger having to perform the ceremony - but only if he is drunk, Rebecca having to ice the cake after insulting the kitchen staff, and Lilith having to sing to the guests in order to stop them, and Woody and Kelly, from finding out the disasters going on behind the scenes.
Rebecca spots Lilith with another man, and doesn't know whether to tell Frasier. Later, Lilith confesses to Frasier that she cheated on him - once. Frasier is devastated, and after he and Lilith talk about it, Frasier asks Lilith to tell her lover the affair is over. Lilith goes to see him - and then comes back saying she wants to leave Frasier. Meanwhile Sam hires a bouncer named Tiny, but can't bring himself to fire Tiny when nobody wants to go near him.
Lilith informs Frasier that she wants to spend a year away from him, sealed in a biosphere with her lover. Frasier reacts to this like any trained psychiatrist - he steps onto the ledge of Melville's and threatens to jump if Lilith leaves him. Lilith and Sam manage to talk him down, but Lilith insists their marriage is over. Once Lilith has gone, Frasier's friends rally round in support of him.
Frasier decides to start dating other women now that Lilith has left him and Frederick, and makes a date with his secretary, Shauna. He arrives at Shauna's house only to discover that Shauna is just using him to annoy her parents as they are not letting her see her boyfriend - who then turns up unannounced. Meanwhile, Cheers is hosting a family reunion, and Cliff and Norm are videotaping it, but then discover the camera was never switched on and have to try and recreate the video without anyone realising.
Frasier is upset when he hears that Lilith now officially want s a divorce. The staff at Cheers decide to hold a "happy divorce" party to cheer him up, and at the party, whilst Woody drinks too much and becomes a mean drunk, Frasier gets drunk. Afterwards Rebecca drives him home, but they end up in bed together. However, first the gang pop around to check Frasier is OK - and to watch "The 3 Stooges" - but just when they leave, who should show up but Lilith, who has escaped from the eco-pod...
After returning to Boston only to discover Frasier in bed with Rebecca, Lilith comes to Cheers to seek Sam's advice. Frasier comes after her, and Rebecca shows up as well to explain. Frasier says he can't take Lilith back after what she did - just as her lover, Dr Pascal, shows up and takes the gang as hostages unless Lilith returns to him. When Paul and John Allen Hill show up and also get taken as hostages, Lilith has to persuade Pascal to let them all go, and that she doesn't want to go back. Plus will she reconcille with Frasier?
Sam locks his keys in the bar, meaning he can't go home. He goes to Carla's to get her keys to the bar, but Woody has them. Carla offers Sam her couch for the night, but John Allen Hill is there so Sam heads off. He visits the houses of Cliff, Norm and Frasier before finally ending up in Rebecca's house.
After Woody, Kelly and her father Lloyd arrive at Cheers talking about classical music (they'd been to a symphony), Rebecca joins in the conversation and impresses Lloyd. He invites her to a society function. Rebecca thinks it is a date and is thrilled to bits - but is in for a shock when she arrives. Meanwhile Esther Clavin has been put in a retirement home by Cliff, but whilst Cliff feels guilty, the others think he has murdered his mother.