Michael feels abandoned when Stephanie leaves for the weekend to host a baby shower at the Vanderkellen mansion, and he attends a Beaver Lodge dinner with George out of desperation; Dick and Joanna's traditional anniversary picnic is threatened when they are unable to find authentic blue cheese.
Dick considers dropping out of a typing class being taught by his tyrannical sixth-grade teacher when the man refuses to acknowledge Dick is no longer an unruly eleven-year-old without a future; Michael develops an even more cocky persona after attending a Tom Cruise film festival.
After interviewing for a coveted network job, Michael comes to the realization that the only way he can advance his career is to do something he has never tried to do before: produce quality programming; George becomes obsessed with naming a large rock that he, but no one else, thinks looks like a duck.moreless
Joanna throws Dick out of the bedroom following an argument on a night that the inn is booked full. After exhausting all other possibilities, he resorts to spending the night with Larry and the Darryls.
Joanna accuses Dick of never being spontaneous, but soon realizes that might not be such a bad thing when they become stranded at a flea bag motel in New Hampshire; Michael suffers emotional trauma when he crashes his beloved car into a mailbox.
Following his idol Edwin Newman's last minute "Vermont Today" cancellation, Dick takes out his frustrations on an inept guest, which in turn gives Michael a new, confrontational vision for the show; Stephanie goes to great lengths to get the word "cupcake" for her personalized license plates.
Dick reluctantly agrees to represent Larry, Darryl & Darryl at trial following Officer Shifflett's discovery of their neighbor's missing cow in the basement of their cafe; Michael and Stephanie are devastated to find out a couple more adorable than them has moved into town.
George tells Stephanie they are no longer friends after she goes shopping instead of fulfilling a promise to help him pick out clothes for a dance. Joanna reveals she has an intense fear of eye doctors.
George takes matters into his own hands when the town board rejects his bid to repair a storm-damaged bell tower constructed by his grandfather; Michael rents The Wizard of Oz to overcome his fear of wind.
Dick's old college sweetheart Diane visits the inn for a weekend of skiing, and causes sparks to fly when she reveals Dick had proposed to her; George fears he has made himself obsolete when he runs out of things to do.
In an effort to get Larry to leave her alone, Stephanie orders Michael to help Larry introduce himself to a young woman who works at the bakery; Dick finds himself having to apologize for actions he took in Joanna's dreams.
Dick reluctantly allows George to accompany him to a high-class literary party in New York, and is stunned and jealous when George becomes the life of the party; Joanna stays home to host is visit from a friend who never shows up.
Dick, the former advertising executive, finds it a hard pill to swallow when his idea for a library fundraiser is rejected and Joanna's is unanimously applauded; A guest claims to have stayed in the inn many times since 1775 as various reincarnated lifeforms.
Dick's plans for the perfect Thanksgiving are thwarted first by the Inn's faulty electrical wiring, then by Stephanie's discovery that her favorite childhood toy has been discarded.
Larry is devastated when his brothers begin spending all their time with a new friend they met at a hollering contest; Tired of all the bad parties in town, Michael and Stephanie plan to host their own.
Stephanie decides she must change her ways to win back Michael's heart; Dick is outraged that the only mention of "Vermont Today" in the station's three-hour anniversary special is a short blooper clip.
Michael becomes enamored with a temporary assistant while producing a clip show to celebrate the station's anniversary; Larry and the Darryl's feel their "Anything for a Buck" business is threatened both by inflation and George's generosity.
Everyone in town but Dick believes Joanna is having an affair with a classmate in her wine tasting class; Stephanie's life is upended because her hairdresser has moved away.
In the midst of a midlife crisis, Dick decides to move to Oklahoma after reading a book about how to be a cowboy; Stephanie secretly hires Larry and the Darryls to do her chores.