We finally found out who Sam's telephone proposal at the end of the last episode was to - Diane! But Diane fears that Sam is meerely on the rebound after breaking up with Janet, so asks him to repeat the proposal in a more romantic occasion, but when he does (on a boat), she refuses, causing Sam to make her walk the plank. Later Diane says she does want to get married, but Sam has now retracted the proposal.
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.
The gang insists on getting in on Norm's new business investment then complains bitterly when it looks like a washout.
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 proposes to Diane again and ends up charged with assault and battery when she turns him down again.
Sam finds himself in a bind when Diane falls in love with an engagement ring costing ,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 hug 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 hug 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 and Lilith invite Sam and Diane over for dinner to celebrate their first week of cohabitation. But things start going wrong when Lilith finds out Frasier and Diane were engaged, and she locks herself in the bathroom. Then Sam and Diane have an argument as well. Meanwhile Cliff agrees to babysit Carla's kids.
Diane badgers a noted British marriage counselor into seeing her and Sam for a pre-nuptial session, then refuses to heed his advice.
Sam's goddaughter Joyce Pantusso (the late Coach's niece) has come to Boston for a visit. Not wanting her to get into trouble, Sam asks Woody to help her out and show her around - but Woody and Joyce have a surprise for Sam when they get engaged!
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 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.