Six months has passed since Diane left Sam at the alter. Sam had since sold the bar to a corporation and bought himself a sailboat where he had been living until it sank. Now he's returned to Cheers and is looking for a job.
Sam gets the chance to fill-in for his old buddy on TV for a week as a sportscaster on the evening news. But to do so he must dodge his duties at Cheers.
Eddie proposes to Carla and wants her to meet his mother. The get together is a disaster when she takes an immediate disliking to Carla and wants the wedding called off. Elsewhere, Rebecca nervously awaits the arrival of her boss.
It's up to Sam to get Carla and Eddie back together after Eddie's mother did not approve of his choice of brides.
Having had a fallout with Lilith, the gang tries to convince Frasier that Rebecca wants him. Meanwhile, Rebecca removes Sam's picture and replaces it with one of her own.
After Norm is alerted by Rebecca how much his bar tab has amassed, he works it off by painting her office for her.
Cliff's mom is ready to sell their family home to a developer who wants to build a convenience store on the site. Meanwhile, after discovering Rebecca's college nickname, "Backseat Becky," the gang want to learn how she got the name.
Sam and Woody participate in a charity auction but are not too happy after finding out who bought them.
Woody takes the role of Mark Twain in a local theater production, and meets an older woman while still in his makeup which he begins dating.
Sam is asked by Rebecca to attend a company function with her to prove to Evan Crane that she is not a lesbian. Meanwhile, Frasier comes down with a bad case of the hiccups.
Cliff creates a monster when he moves into a singles apartment complex and meets Sally, a very plain looking woman. Cliff explains to Rebecca that she won't go out because of her looks, in which Miss Howe suggests she gets a makeover. Pleased with her new face, Sally becomes a hit at Cheers, making Cliff wishing she was back to her old self. Meanwhile, Rebecca has begun smoking again and makes a pact with Sam, if she ever smokes again, she will sleep with him.
The gang finds themselves depressed on Christmas Eve, with Rebecca keeping the bar open late, Carla wants to be home with Eddie, and Woody is away from home for the first time during the holiday season. When Sam is invited to a late night dinner at Rebeca's apartment, Sam becomes desperate to find her a gift.
No one will believe Woody when he says he was hired to play a tiny role in an episode of Spenser: for Hire. Meanwhile, a disagreement between Norm and Cliff over the paint job Norm has done in Cliff's mothers apartment, has a chimpanzee doing the same work Norm has just completed.
A company picnic at Evan Drake's home ends up making Woody buddies with the boss due to his taking the fall for Rebecca who has broken one of Evan's vases.
With Carla on maternity leave having given birth to twins, her daughter Annie fills in, and Mr. Drake has hired a pretty young girl to work at the bar causing jealous feelings for Rebecca, who is unaware that the girl is his daughter.
Sam is invited to bring a guest along for a weekend on Evan Drake's yacht. When Rebecca finds out, she insists that Sam brings her along so she can get closer to Evan.
Sam and Rebecca give Frasier and Lilith their bachelor and bridal showers. While Frasier's promises to be a party to remember, the fun suddenly stops when the stripper ends up being one of his patients. Meanwhile, Lilith's party becomes a blast, so much so that a drunken Lilith misses her call from Frasier she had asked him to make, putting fear in his mind that she has run off with the male stripper.
While Evan Drake is in Europe, Norm has been hired to paint the inside of his home. When Rebecca finds out she badgers Norm into letting her look around Evan's place. But when he comes home unexpectedly, she must find a place to hide.
Eddie has been cut by the Penguins and gets a new job skating as a penguin in The World of Ice show. But Carla can't go to visit him because she is afraid to fly. Frasier decides to hold a workshop for others who have the same fear, ending with a plane trip. While the patients are calm aboard the flight, their comments have Frasier freaked out. Meanwhile, Rebecca awaits the arrival of Murray Treadwell, a local restaurant critic, hoping to receive a positive review of the bar since taking over the management.
Evan Drake promotes Sam to an executive position, which upsets Rebecca. She figures out that Sam only got the nod so he could be a ringer on the corporation's softball team. Despite wanting to throw this back in his face when the season ends and Sam is fired, he tells Rebecca how his father said he was proud of him, causing her to rethink her plans.
With all the crew asking for raises, Rebecca confides that the bar may be shut down since it is losing money. The gang devise an idea to raise money by raffling off a cruise. But an error by Woody has the winner being number 66 or 99, and both patrons threaten to sue.
When Carla learns she is about to be a grandmother and becomes depressed, Lilith and Rebecca throw a slumber party in an attempt to cheer her up.
The Cheers gang declares war on a rival bar, Gary's Old Town Tavern, and steals their bowling tournament trophy.
Sam and Woody square off to see who can kiss Rebecca first.
Rebecca goes to great lengths to try to get some time alone with Evan Drake before he moves to Japan.