Sam couldn't stop the wedding, but Frasier tells him that Diane left him at the altar and is now working at a convent. So Sam visits Diane to ask her to come back to Cheers. Meanwhile, Woody comes to Boston to look for a job and becomes Cheers's new bartender after his pen pal Coach died.
The gang at Cheers flies Woody's old girlfriend in from Indiana to visit, and it becomes obvious that when they're together they use binge eating to curb their sexual urges. Meanwhile, Frasier takes a job at Cheers to make Diane feel guilty.
Through a strange twist of fate, Diane meets a cultured, intelligent man who appears to be perfect for her. But she eventually wants to dump him because she thinks he's not attractive enough for her.
Sam accidentally convinces Carla's son Anthony to get married, Cliff is convinced that he's grown a potato that looks like Richard Nixon, and Diane blows her opportunity to get a part-time position at the university.
Diane dreams that "Andy Andy" has escaped form a mental institution and is coming to kill her. But when she wakes from her nightmare, "Andy Andy" shows up at the bar to ask a favor.
Sam loans Diane $500 to buy a book autographed by Ernest Hemmingway. She later gives the book to Sam as collateral until she pays back the loan, but Sam accidentally destroys it.
The guys at the bar feel sorry for Carla because nobody has responded to her newspaper singles ad. So they start sending her romantic responses from a fictional airline pilot.
Norm's neighbor tells him that she suspects that Vera is having an affair with her husband, and Sam must apologize for degrading Diane on a call-in radio show.
Cliff bonds with his long-lost father until he learns the real reason why he came back to see him. Meanwhile, Sam suspects that Diane intentionally sabotaged his date with a smart, cultured woman.
Diane uses Sam as a case study for a paper in her Human Sexuality class, but she paints an unflattering picture of him. Meanwhile, Woody challenges Carla to a sports trivia contest, and Cliff grows a unique squash.
Diane convinces Sam to go to Frasier with fake depression symptoms so that Frasier can analyze him and get his confidence back as a psychiatrist. But Frasier comes back with a diagnosis that Sam's depressed because he's still in love with Diane.
Diane rejects Cliff's request to be his date for the postman's ball, so he asks Carla, who will go with him--for a price. But what will he do when Diane reconsiders and decides to go with him?
Norm is up for a promotion at work when he finds out that his competitor is having an affair with their boss' wife. Will he use this helpful bit of information to guarantee that he gets the job?
The guys at the bar feel guilty for constantly teasing Diane and not inviting her to their gatherings, so they try to make up by taking her to her favorite opera.
Sam hires a new bartender and appoints himself as host/manager of Cheers. But when his new strategy goes belly-up and he is forced to return to the bar, somebody has to be fired.
Sam begins dating a city Councilwoman who is running for reelection, but Diane is convinced that she is just using him and will dump him after she is reelected.
Councilwoman Eldridge tells Sam to fire Diane because she's insecure about having one of Sam's former lovers working at the bar. However, Diane accidentally overhears the conversation and tries to beat him to the punch.
Councilwoman Eldridge presses Sam for a marriage proposal, but Sam remains noncommittal. She then dumps Sam after he and Diane create a scene at her press conference. The incident leads Sam to a proposal--but to whom?