After his wife leaves him and he's fired from his job at a high-profile New York city law firm, Ed Stevens moves back to his small hometown of Stuckeyville where he buys the local bowling alley and attempts to win the heart of his high school crush.
Ed and Carol stumble through the first days of their changed relationship; Mike and Nancy have their hands full with a new puppy and its dishonest breeder; Eli is bewitched by an attractive and talented pie maker.
The first weeks of the new relationship between Ed and Carol are seen through the lens of his cousin Benny, who's filming a documentary for his final film school project; when Carol's lease is up, she and Ed decide to move in together; while mugging for the camera, their friends comment on Ed and Carol, and the nature of romantic relationships in general; as time goes on, and familiarity begins to breed indifference and conflict, Ed learns an important lesson about relationships from his high school driver's ed teacher and Carol gets a crucial insight into Ed from Mike; Molly teaches Warren a lesson about punking one-upmanship.
Ed & Mike buy a racehorse. Carol faces trouble with the school board and Molly when she suggests to Warren that college may not be for him. Warren pursues his dream of being a TV host on local cable access.
Carol hides her old love letters concerning a man from her past from Ed. Ed breaks down and reads the letters and pays the guy a visit to check him out. Mike and Nancy are concerned that their baby will eventually learn of past indiscretions and go down the path of revisionist history. Meanwhile, an academic historian questions the role Stuckeyville's founder played in a Revolutionary war battle that is reinacted every year. Ed tries to help General Stuckey's descendant (the town historian/barber) maintain his family's integrity while saving Stuckeyville's historic reputation.
Mike and Nancy devise a series of bizarre tests to determine which of their friends would make the best guardian for Sarah if anything were to happen to them; Phil creates the perfect farewell of a 21 pin salute for an eccentric customer who breathes his last at Stuckeybowl; Molly meets an adventurous new man who literally sweeps her off her feet and into the air; Ed represents a man being sued by his father for the cost of his undergraduate and dental school tuition after he quits his internship because he hates being a dentist.
After a former student encourages Carol to interview for a writing job at the magazine where he works, she sets out for New York City, accompanied by Ed; at Molly's request, Warren and Mark escort a new student around school and find that the new kid isn't the only one with something to learn; Carol is sent out to complete a test assignment and does so well that she's offered a full-time writing position; Dr. Jerome and his granddaughter do a little stealth psychological testing on Mike; after some reflection, Carol decides to accept the job offer and relocate to New York City.
Afraid that their relationship won't survive if they live apart, Ed decides to join Carol in New York and puts Stuckeybowl up for sale; feeling that he's losing his best friend, Mike tries unsuccessfully to make a new one; after Ed's client wins an arbitration that prevents his long-time friend from dissolving their partnership, Ed urges him to think both inside and outside the box to discover a solution that works for both of them; Molly comes to crossroads in her relationships, and realizes that neither Sean nor Ted is the right man for her; even though Ed guarantees that they will not lose their jobs, the crew at Stuckeybowl pulls some pathetic stunts to sabotage the sale until Ed decides to make them Stuckeybowl's new owners; Warren sees Carol off in high style; at their going-away party, Carol realizes that she shouldn't tear Ed away from Stuckeyville, so they agree that she'll go to New York and Ed will rack up frequent flyer miles visiting her.
Several Stuckeyville stalwarts seek a sympathetic ear to help them resolve relationship roadblocks: Ed sees out a therapist with a unique background to help him deal with his new long-distance relationship; Eli uses his physical therapist as a sounding board about the possibility of a future romance with Jennifer; Molly gets some expert guidance counseling from Nancy about her flirtation with an unlikely suitor.
Ed is planning an elaborate proposal in New York, but when Carol returns to Stuckeyville to find out how they stand, he must come up with another plan. Mike's parents visit and his dad drives Mike crazy. Plus he wants to deep fry the turkey. Eli, afraid, that Jenny will date someone else, arranges a charity Thanksgiving dinner at StuckeyBowl and enlists her help.
Ed asks Carol's father for his permission to marry Carol, while Mike and Nancy argue over the needed rennovations to their fire-damaged home.
With only a few days left until Christmas, Ed's getting ready to move back to New York with Carol, however an unexpected "friend" returns from Ed's past. In the meantime, Mike and Nancy are anxious to get back into their home in time for Christmas, and Mr. Hagadorn's annual Christmas yard display is under attack from a neighbor.
After a disastrous meeting with the wedding planner, Carol wonders if she and Ed shouldn't elope; Ed soon regrets the advice he gives Mr. Mazula when his former teacher asks him to draw up a prenuptial agreement; Nancy and Mike decide that he needs to make more decisions around the Burton household, including planning the engagement party for Ed and Carol; presented with the opportunity to be represented by a literary agent, Carol struggles against time and writer's block to produce three chapters of a novel; when Mike's decision making ability melts down over magazine subscriptions, Nancy steps in to save the day and the engagement party; after Molly helps Carol realize that playing it safe is getting in the way of her writing and her wedding plans, Carol gathers up her courage and removes the obstacles to both.
Ed's ex-wife, Liz is back in town and tries to get Ed to help her get a new restaurant up and going. Meanwhile, Eli is trying to come to grips with his girls 'desires'
Carol is concerned that Liz and Ed still have feelings for each other when Liz returns to town with yet another business proposition for Ed; Mike's eager anticipation of the arrival of Gunter, the foreign exchange student that the Burtons have agreed to sponsor, turns to disappointment when Gunter seems more interested in hanging out with Nancy than playing sports with him; Eli's concern about the closing of the community center prompts him to challenge a radio talk show host, and he does so well that the radio station offers him a tryout when the host gets the flu; Molly urges Carol to talk to Liz after Liz gives Ed an inappropriately expensive watch; Eli continues to use his stint on the radio to advocate for the community center and enlists Ed's help in convincing the City Manager to keep it open; Mike discovers that he couldn't be more wrong about Gunter's interest in women after Gunter tries to kiss Nancy; Liz gives Ed the inside information he needs to help Eli expose the corrupt
As Carol and Ed are finally seeing Liz off, they get mugged, leading Ed to question whether he could have prevented it; Russ pays Mike and Nancy a visit after his wife kicks him out for cheating; Phil sets up a ridiculous and elaborate security system in the aftermath of the robbery; Kate offers Eli another gig at the radio station, but Jennifer isn't happy about Eli's spending time away from her; Liz's continued presence in Stuckeyville as a result of the mugging begins to wear mightily on Carol, so Ed asks Liz to leave; after Kate is fired for backing up his decision not to grant a listener's request, Eli devises a scheme to get her rehired, which dovetails nicely with Russ's plan to win back his wife's affections.
In the days before the wedding, Lloyd is back in town and back in trouble; Nancy and Mike are both under the weather, but not for the same reason; Carol is unhappy, and Ed is impressed, when Stella reconnects with an old flame; Warren's attempt to play a cute trick on a friend fulfills a fantasy from his past, but not in the way he, or anyone else involved, would wish; Shirley and Toby find each other and count the things they have in common; Dr. Jerome finally has something nice to say to Mike and Nancy.
Eli takes pity on Phil's latest get-rich-quick scheme; Warren, Mark and Jimmy create a hilarious Ed and Carol tribute video for the rehearsal dinner, but Shirley is the one who really brings down the house with a special song; Mike feels a little lost as the best man in the face of the extensive groomsman experience and contacts displayed by Ed's cousin Mitch; Molly opens the door when a possible opportunity comes knocking; Ed gets a behind-the-scenes inspiration for a wedding day $10 bet from a surprising source; Ed and Carol hatch some truly hairbrained ideas in their quest for the appropriate theme for their wedding until Ed's inspiration leads them to the perfect place to start the next phase of their lives.