After the sad passing away of Coach, Sam hires a new bartender in Woody Boyd, Coach's pen pal who has moved to Boston. Frasier arrives back from Europe with the news that Diane left him at the altar for six months of decadent living across Europe and is now seeking renewal in a Boston monastery.
The gang brings Woody's old girl friend to Boston to visit him and Frasier, still not yet confident about returning to psychiatry, 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 hug her.
Although Sam would usually have no qualms over lending Diane money, especially a measly 0, that is until he witnesses he recent spending spree and that she has used the money to purchase a book.
Carla's ad in the personals has not been answered, so the guys decide to make up a man for her. Airline pilot Mitch Wainwright is created as a means of raising her spirits, but she becomes obsessed with the 'man'.
Norm fears Vera may be having an affair with his neighbor and Sam wastes his time as a radio sports commentator apologizing to Diane.
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.
After making a fool out of the gang at Cheers with her psychology-class experiment in paranoid behavior, it's Diane who may become a better case subject as she nervously awaits their revenge.
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.
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.
Norm has some dirt on the competition for a promotion at work, that could give him the position.
After trying (and failing) to hit on a pretty female customer, Sam feels like he is over the hill and challenges Woody to a racquetball game. Unfortunately Sam ends up hurting himself and has to take a trip to the hospital.
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.
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.
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 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.