Caroline and Richard's big night finally arrives, in the form of a romantic weekend booked in the perfect room at the perfect country bed and breakfast. What's wrong with this picture? Naturally everything: Richard's choice of the perfect negligée for Caroline to wear gets switched for Del's brother's barbeque apron; their room is given away to another couple who have gotten married after not seeing each other for 30 years; and the bed and breakfast is run by a bitter, bickering pair of neurotics who ultimately throw Caroline and Richard out. But Richard saves the day by getting Annie and Del to turn Caroline's apartment into a romantic fantasyland - which, we learn in the coda, they enjoy for several consecutive days...

Del and Caroline participate in the company's mentoring program, but Caroline's adolescent charge Stan develops an embarrassing crush on her, while Del's turns into a teenage fixer who takes over Del's professional and personal lives with impressive competence. Meanwhile, Reg tries to convince Richard to sell his art, but the results are disastrous: a coffee house show is a fiasco, and when Richard desperately tries to emulate a subway hawker and sell his works to consumers, he is busted by an undercover cop who confiscates his art.

Caroline's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy refuses to leave, forcing Caroline to return to Wisconsin, where she is surprised to learn that her former boyfriend Randy will be her new tenant. Meanwhile, Richard has his hands full in New York when he agrees to take Caroline's place by caring for Annie (who is sick) and Del (who thinks his girlfriend may be cheating on him).