The Cheers regulars are finding it hard to adapt to Sam and Diane's new relationship. Diane is also having problems with this, which easily shows after she kicks Sam out of her apartment only after 5 minutes of him arriving.
Carla goes into labor at the bar, and her sister comes to fill in for her at the bar. She begins to become interested with all the guys at the bar, espically Cliff. Cliff decides he wants to marry her, but doesn't know that she's been fooling around with every other man at the bar. Norm ends up telling Cliff it isn't a good idea for him to marry Carla's sister.
Diane wants to go to a speech at a college, but in order for her to do so, she needs to change schedules with Carla. Diane sweet talks Sam into convencing Carla that switching one night with her wouldn't be that bad. Carla refuses to make her point, that Diane gets away with things more than the rest of them would. Diane thinks this is interfering with their relationship, so she quits her job at the bar, and goes on the search for a new job. She comes back in a few weeks with a job at a publishing house. Diane has told Sam that her boss wanted to talk with him, to ask him a few questions about Diane, but the questions her new boss askes Sam are far from professional. Diane gets up-set that all the job offers she has gotten, all had sexual strings attatched.
Andy Andy is back in action. He comes into the bar, harmlessly asking for a drink, then the next thing you know, he's pointing a gun at the bar, demanding all the money in the cash register. They soon find out that Andy isn't a bad person at heart, and that his dreams are to become an actor. Diane decides to help Andy with his dreams, and does a scene from a play infront of her old college professor. While getting ready before the performance, Andy see's Diane and Sam kiss. He becomes angry and actually trys to strangle Diane in the scene they do together.
Sumner comes back to Cheers, hoping to win Diane back. But he fails miserably as Sam reads 'War and Peace' to impress Diane. Diane soon has to choose between Sumner and Sam. She chooses Sam, of course!
A man named Hank comes into Cheers, and becomes interested in Carla. Diane thinks it's sweet, so she decides to help out, and convinces Carla that he's not that bad. She agrees to go out with him, until she finds out what's wrong with him. After a few dates, things seem to be going well, until Carla dumps Hank for no aparent reason. Diane and Sam soon find out that Carla was right. Hank has a serious heart condition and too much excitement could hug him.
One of Sam's old friends, Dave, comes into the bar hoping to get the old, skirt chasing Sammy Malone back. But what Dave doesn't know is that Diane and Sam are going together. When Dave finds this out, he makes a bet that he can break them up in the next 24 hours.
An old friend of Sam's comes into Cheers, hoping to get Sam as a coach for his little league baseball team. Sam tells his friend that he's been too busy with the bar and Diane. Coach comes up with the idea for him to be the coach of the baseball team, and Sam thinks it's a wonderful idea. But Diane on the otherhand, does not. She thinks that sense Coach was use to training players in the Major League, she's afraid he'll drive the children away by making them work too hard.
Dick Cavett suggests to Sam that his autobiography might sell well on the market. So him and Diane get to work on it. Meanwhile an old flame of Vera's comes to town looking to win her back; it's up to Norm to confront him about it.
Diane gets Sam a pair of tickets to a fight Sam has been wanting to see. Sam is so happy, he blurts out the phrase, 'I love you'. Diane takes it seriously and is totally taken back by what Sam had said. Diane goes to tell Sam that what he told her really made her happy, and he thinks nothing of it. Diane then proposes that they think about their relationship. If neither one of them can come up with an explination as to why they are together, Diane thinks they should call it quits. A week later, Sam and Diane still can't figure out what their relationship means, and Sam can't bring himself to tell Diane that he loves her sense he used the phrase so casually.
One of Diane's friends, Heather Landen, comes to Boston for a visit. Diane brings her over to the bar and introduces her to everyone. Heather is very nice to everyone at the bar, espically Sam. Sam starts to worry that Heather is getting a little too friendly, and warns Diane about it. Diane thinks Sam is just over reacting, and invites Heather to dinner with her and Sam. Once things start getting a little too friendly at Diane's apartment, Diane loses it and confronts Heather about it. Heather explains she's just a friendly person and her intentions were to make friends and not steal her boyfriend.
A man comes into Cheers, who only has 6 months to live, and who is oddly rich. Diane and Sam comfort him and talk to him. Sam lets him work behind the bar, since it's something he's always wanted to do. When it's time for him to leave, he leaves a will which says that Sam gets all of his money. Everyone starts to fight over the money, and Diane convinces Sam to destroy the will, because it's making everyone go crazy.
Nick comes into the bar with his new Fiance. Carla is desperate to find somenoe to go to the wedding with her to show Nick up. She begs Sam, and Sam and Diane agree. When Nick sees Sam and Carla together, he secretly now wants her back. Sam and Carla go to the wedding, and have a great time. Later that night, Nick comes back into the bar and kisses Carla, hoping it will make some sparks between them again.
Norm is officaly out of work, and is desperate to find a new job. He's been working as a dish washer, when he can get a much better job. Diane comes up with the great idea to have Norm as Sam's accountant. Sam is a little protective over his money, and doesn't think it's a good idea to do business with friends. Diane convinces Sam to hire Norm and he does. But, when Norm finds out Sam had never fired his old accountant, things get a little rough in their friendship.
Diane and Sam are spending a romantic evening together, when Coach barges in on them. Diane and Sam are desperate to find Coach his own girlfriend so they can have time for themselves, but the plan backfires when Diane and Sam have to admite that the reason they set Coach up with somebody is that they don't want him hanging around them so much.
Cliff doesn't get along very nicely with a man that comes into the bar. He pushes it far enough to where he wants to fight Cliff. Cliff, being the coward he is, trys to back out of it. But when it's time to face the music, Cliff shows them some of his fighting skills that he doesn't have, and ends up asking Diane to bring him to the hospital.
Coach has ordered yet another item from a con man. It's a weight telling fortune machine. Carla is spooked by the machine when everyone's fortune comes true. Diane doesn't believe in it, until she gets a fortune that relates to her and Sam.
Sam wants to go on a ski trip with his old friends, and tells Diane that his uncle died so he could go up to Vermont without her knowing. Carla trys to convence Diane that it's just a bluff so Sam could leave. Diane starts to believe Carla and confronts Sam.
One of Coach's old friends die. He's so upset, he wants to have a funeral in Boston for him. Sam doesn't think it's a good idea, but doesn't tell Coach. Instead, he tells Diane that Coach's friend had an affair with his wife. Coach over hears the conversation, and becomes furious.
After an attractive new client begins to seem interested in Norm; the gang tries to get him to pursue her.
Sam is asked to pose in a magazine as an eligible bachelor and agree's to. Diane is offended by this (because they are dating right now) and does not take it lightly. Meanwhile, Semenko, a famous artist, has stumbled into Cheers and wants to make Diane the subject of his artwork.
After seeing the half done portrait of Diane Sam forbids her from posing for him ever again. But of course, Diane will not take this obnoxious order.