After Coach's death, Sam hires a new bartender in Woody Boyd who was Coach's pen pal. Frasier arrives back from Europe after Diane left him at the altar. He tells them that she had six months of decadent living across Europe and is now seeking renewal in a Boston monastery.
Woody's old girlfriend comes to Boston to visit him. Frasier decides to pay his bar bill by working as a janitor.
After Diane fantasizes about the owner of a coat left at Cheers, Sam pressures her to ask the coat's owner for a date no matter who the owner turns out to be. When the owner comes to claim the coat, Diane tries to wiggle out of her "dream date". Meanwhile, Norm and Cliff work together on a high school science project.
Carla worries that her son, Anthony, is contemplating getting married, even though he is still a teenager. She heads to Sam for help who tries to convince Anthony being a bachelor is far better than being a husband. Meanwhile, Diane has an interview with her former fiance, Sumner Sloane.
On a dark, stormy night, Diane awakens from a nightmare in which she fears that Andy Schroeder, the crazy date who once tried to strangle her, has escaped from the home for the criminally insane and is coming to kill her.
Norm and his neighbor's wife hire a private detective when they assume that their spouses are having an affair together.
Cheers and Gary's Olde Towne Tavern are set to compete in their first ever athletic competition against each other, and the guys discover that bowling is not up their alley. But they find a reluctant hero in Woody, who doesn't want to compete.
Cliff's father comes to Cheers to give him an important message, but Cliff is reluctant to identify himself to the man who left his family behind. Also, Sam is dating a woman with a brain, and tries to keep her from meeting Diane.
Sam is proud to be the subject of Diane's psychology paper for school titled, “Don Juan Syndrome,” until he realizes what an unflattering picture she has painted of him.
Woody has had a remarkable winning streak playing the Cheers football pool. So the gang convinces him to place a bet with a real bookie. But no one expected that he would bet all his life's savings on the game.
The gang convinces Sam to give something to the annual charity auction, and is devastated when no one bids on his authentic jersey. Meanwhile, Norm tries to impress a potential client and his wife, but soon realizes that none of them have anything in common.
Frasier has been hitting the bottle hard since his break up with Diane, and Sam wants to help him, having been there himself. But Sam has no confidence in Diane's plan to restore Frasier's self respect.
Cliff finds himself in an unusual situation when he has two dates for the annual postman's ball. He asks Sam for advice when he needs to drop either Diane or Carla.
After Frasier is dumped by his date, Sam sets him up with a woman who "cannot say no" to anyone.
Norm has some dirt on the competition for a promotion at work, that could give him the position.
In an effort not to look old in front of the guys, Sam winds up giving himself a hernia, which he tries to keep secret.
After finding out that Calra's ex-husband is going to compete in a dance contest with the younger Loretta, Carla tries to enlist Sam as her partner.
Sam and Diane find themselves in a matter of life-and-death when the pilot, Diane's ex-boyfriend, dies during the trip.
The guys at the bar feel bad for always shutting out Diane from their activities and decide to attend anything she chooses...which happens to be an opera.
Sam has decided to become the host/manager of Cheers, and therefore will need to hire a new bartender. But after the idea fizzles out, Woody fears he may lose his job.
Sam falls for city councilwoman Janet Eldridge, as she stepped into Cheers to campaign. A jealous Diane decides to join her opponents side, believing she is out to steal Sam away and then dump him after the election. Frasier joins the opposition too, in hopes of getting Diane back.
Diane feels even more jealous now that Janet and Sam's relationship has grown stronger. Janet believes Sam needs to cut all ties to his past, which means he must fire Diane, a conversation she overheard. But Diane beats him to the punch and quits. Meanwhile, Norm fears that Vera's visiting sister will once again try and seduce him like she did on her last visit.
Janet has won the election and gathers the press to Cheers to give a speech. Diane shows up and fires a few fastballs by he in the form of questions, causing Sam to remove her from the bar. Janet has been pressing Sam for a marriage proposal, but seeing a lack of commitment in his actions, decides to dump him. This causes Sam to call someone on the phone and propose. Meanwhile, mush to his fears, Vera is called away leaving he and Donna alone.