Sam becomes frustrated when Diane refuses to accept his marriage proposal over the telephone, and then agrees to meet her for a romantic evening and then still rejects him.
Since Diane said no to his wedding proposal once too often, Sam says he will never ask her again. He brags that he has set up a romantic weekend with another woman at Cape Cod, which entices Diane to follow him. Although alone, Sam won't mention that his date has returned home early.
Cliff makes plans of becoming a rich man someday by introducing his mom to a rich bar patron. But the man explains that when he dies, he's leaving all his money to charity.
Diane helps Frasier and Dr. Lillith Sternin get together after noticing a chemistry between the two. Meanwhile, Woody invites Norm and Cliff to a fishing trip, which they reluctantly attend.
Carla buys a new house and later discovers it is on top of a 17th century prison graveyard. So Cliff is recruited to spend the night there to prove there is nothing to fear.
Norm gets the whole gang involved when he invests in a combination laundry and tanning salon.
Woody becomes obsessed with creating a new drink. After many failures he hits a tasty new concoction...now if he can only remember the ingredients. Meanwhile, Diane and her new beau have reservations at a new "in spot" of Boston, named The Cafe. Sam believes he should bring his latest date there also.
Sam becomes jealous when Diane announces that she has been doing some part-time teaching and one of her students is in love with her. Also, Cliff wants to join the Knights of the Scimitar, an exclusive lodge. He also wants the gang to join but only Norm agrees, in hopes of making new business contacts. But a rule will keep him from doing so.
Diane invites everyone to Carla's home for a Thanksgiving dinner, only to wind up with a frozen turkey and burnt peas as their meal.
Diane receives a rejection letter from a literary magazine, touting her work as promising. Sam believes that he would receive the same letter if he sent a poem in to the same magazine. But when his work is accepted, Diane goes all-out to prove his poem was plagiarized.
After receiving a "Dear John" letter from Beth in the mail, Woody searches through Sam's legendary black book to find a woman to show off as his date.
Diane announces that she has been taking ballet lessons at a community college class with the world renowned Madame Lihkova. She must submit a video tape for her final exam, which the gang get a hold of and its harsh critiques. Frasier rewrites the message to something positive, which swells her head to the point of wanting to audition for the Boston Ballet.
Sam winds up in jail for assault and battery after proposing to Diane one more time.
Sam finds himself in a bind when Diane falls in love with an engagement ring costing $5,200. Norm suggest using his friend to make a fake ring for a fraction of the cost. But the pressure is too much for Sam and he buys the expensive ring, switching it before Diane finds out. After revealing his secret, Diane becomes so upset that she tosses the ring out the window...unaware that it's the real ring.
When Loretta catches Nick cheating on her, Diane and Carla come to her side for comfort. But when Sam stands up to Nick, he believes that Sam and Loretta are now a couple and vows to steal Diane away from him. Meanwhile, Frasier struggles in a game of chess against Woody.
Eddie Lebec, a recent addition to the Boston Bruins hockey club, falls for Carla. Meanwhile, Diane is named foreman of a murder trial and is sworn to secrecy, but spills the beans to anyone who will listen.
Eddie was the hottest goalie in hockey until he and Carla became an item. Meanwhile, the defendant in Diane's murder trial shows up at the bar.
Sam and Diane decide to allow each other one last fling for 24 hours before their wedding day, but neither take advantage of the situation.
Diane asks for some time away to visit a Buddhist monastery to get her life straightened out. Meanwhile, Cliff is all set to sue the owner of a dog which left him with a bite on his leg, but gets cold feet after seeing the voluptuous beauty.
Frasier shocks the gang by announcing he has asked Lilith Stern to move in together, and invite Sam and Diane over for dinner. Elsewhere, Carla enlists Cliff to watch over her children while away with Eddie.
Diane pleads for Frasier's friend, a noted marriage therapist, to take them in for a session, then refuses to use his suggestions.
Joyce Pantusso, Coach's daughter and Sam's goddaughter, has come to Boston for a visit. Sam asks Woody to keep her busy so she won't become bored. But when they come back to Cheers, they give the shocking news that they want to move in together.
Norm lands a job at a prestigious Boston CPA firm, but overdoes his importance to the firm with the gang. So when they come to surprise him at work he becomes caught in a lie. Meanwhile, Woody loses a $20 bill and Cliff just happens to have found one.
Woody finds out that his parents fear his safety in Boston and ask him to return to Indiana. So the gang decide to film a short movie showing the life that he leads each day in hopes of changing their minds.
Sam and Diane find their dream house, but after hearing the story of the elderly couple who live there now, Diane doesn't have the heart to move in.
Sam and Diane's wedding day has finally arrived, as has Dr. Sumner Sloane, along with the news that a producer is interested in one of her manuscripts, but needs to make some changes immediately.