Will is looking for a way to boost his image, so Claude suggests that GNB becomes a paper-free office, not realizing that it will make Owen's job obsolete. Meanwhile, Jeb becomes enchanted by Ramona's rants, inciting jealousy in Lydia, and Kipp drops Will's car key down the elevator shaft and recruits Carl to help retrieve it.

After Claude is told by her date that he's ""not ready for a relationship,"" she catches him at a houseware store with his new girlfriend... so Claude tries to get him to reveal what he doesn't like about her. Meanwhile, Will gets an earring, and Jeb spends an inordinate amount of time Roll-O-Boarding with Owen and Carl, which causes friction with Kipp and Lydia.

When a new guy starts at the office, Claude is oblivious to the fact that he has a crush on her, so she tries to set him up with Ramona. Meanwhile, Jeb and Lydia sneak off to have plastic surgery, but a misunderstanding leads Kipp to believe that Jeb's been kidnapped; and Carl has aspirations of becoming a spy.

Jeb pays Claude to be Lydia's best friend, but when Claude finds out Lydia really likes her she is reluctant to continue taking Jeb's money. Meanwhile, Owen and Carl have a new hobby, walkie talkies, which they can only discuss things over them. Will writes a book, while his ex-girlfriend is his editor.

Mr. Henry a worker at GNB dies in his office, and Claude tries to return his stuff to a family member in Queens. Ramona tries to take Mr. Henry's office but Owen rigs it with special effects to scare her so she wont leave him. And Lydia and Jeb fight over their Halloween costumes.

Assured by everyone that she's a ""shoo-in,"" Claude applies for the GNB management training program... and Kipp applies too. Meanwhile, Jeb learns that Lydia plans to quit working once they're married, so he enlists Kipp to convince her otherwise; and Owen and Carl conspire to make cash by catching fish in the East River and selling them to the GNB cafeteria, but their plan is endangered when Ramona catches on.

Claude babysits Kipp after his laser-eye-surgery and comes to the realization that he may have paid for the procedure with the company's missing funds that Ramona's been looking for. Meanwhile, Lydia is shocked to learn Jeb is hiding a dirty little secret about the fancy hotel she's chosen for their romantic rendezvous. Owen and Carl help Will train for the upcoming NYC Marathon, but they have a difference of opinion on how Will's diet should be handled.

On the day after Thanksgiving, Owen's two mothers pay a visit to the staff at GNB and begin meddling in their lives. Judy (Joanna Kerns) advises Will on his issues with women, while Judith (Valerie Harper) lives vicariously through Carl and Ramona, encouraging them to indulge in her passions for gambling and drinking. Meanwhile, Claude fears that she'll lose her job when Owen blabs about her interview for another job; and Lydia fears that she'll lose Jeb because she accidentally killed his ""Gamma Toots"" at his family's Thanksgiving celebration.

When Claude learns Carl's next ""romantic"" date with Vivian will consist of pizza, she steps in to orchestrate a real romantic night for them. But when Vivian finds out Claude masterminded the date -- which takes place at Claude's apartment - she doesn't appreciate the interference in her budding romance with Carl. Meanwhile, before a shoot for a new photo for the news-van, jealousy rears its head when Jeb learns of Lydia's past relationship with Will; and a trivia contest brings out Owen and Ramona's competitive sides.

Claude is put in charge of organizing the GNB on-air holiday greeting, but is alarmed to learn that there are strict criteria to determine who can represent the company - putting her in hot water with Owen, Ramona and Carl, to whom she had promised an appearance. Meanwhile Lydia refuses to rearrange her holiday plans with Jeb when he announces they must accommodate his son, George, and Kipp and his new girlfriend, Annie, encounter holiday relationship turbulence.

The crew arrives at GNB's annual retreat to discover former human resources representative Schmidtline fired up to point out all their workplace flaws. Claude struggles to lead the group in a team-building task, and when things go poorly, they decide to go AWOL to a casino. Meanwhile, Will and Jeb are left to fend for themselves in the office, but neither can figure out how to make a conference call.

Claude's ex-boyfriend, Charlie, returns to GNB and they decide to give their relationship a second try, so Ramona convinces Claude to buy some sexy lingerie to reignite their passion. Meanwhile, GNB has upped security and reinstated the studio tour, putting pressure on Ramona and Owen to perform as if they had an audience; and Jeb at last seems to appreciate Kipp's work, but he changes his tune when Kipp's great story idea (men with silly beard styles) results in horrible reprocussions.

Carl's girlfriend, Viv, is friendly to everyone except Claude who, she thinks, is trying to steal Carl away from her. But when Carl breaks up with Viv for ridiculous reasons, Claude makes it her goal to get them back together. Meanwhile, Lydia convinces a restaurant to add Jeb's image on their famed wall, which forces Will off the wall.

Claude's boyfriend Charlie temporarily moves in after his landlord pays him ten thousand dollars to move out. However, when Charlie becomes too comfortable with his new wealth and free living arrangements and begins holding auditions for his new band in her apartment, Claude questions her decision . In the meantime, Lydia wants Jeb to take dance lessons to prepare for their wedding, and Owen is the perfect teacher.

Paula Abdul guest stars as a gallery owner who predicts new photographer Owen will become famous, while Lydia and Jeb search for a photographer of their own to shoot their upcoming nuptials.

Will loans his beach house to Claude and Charlie, who find that the uninvited Lydia and Jeb are there. Meanwhile, when Ramona's computer crashes, she finds herself oddly attracted to the dorky software technician; Will's water-massage-table arrives after his departure to Aspen, where he intends to break up with his girlfriend; and Kipp and Carl compete to win the affection of a lovely news producer.

Claude steps in to help Lydia and Jeb with their pre-nup, but finds she may have opened a Pandora's Box. Owen offers to help Claude with Will's fan mail, and forges a relationship with one fan in particular, Louise. But when Louise (played by Joan Rivers) shows up at GNB to meet Will, it could be trouble for everyone. Meanwhile Ramona cooks up an internet auction scheme to get back at Kipp for insulting her.

Claude wins an extreme apartment makeover by the ""Extreme Makeover: Home Edition"" design team at a charity auction. While the designers (and Owen) redesign her apartment, Claude has to spend the night at GNB -- where there is a surprising amount of late night activity and intrigue. Upset over his breakup with Lydia, Jeb bonds with Carl and the two go on a bender; Lydia arrives in hooker attire, claiming that she's fleeing the police; and Kipp makes out with the cleaning lady.

Claude discovers that Jeb and Lydia are pretending to be romantically interested in her and Kipp, respectively, as a means of making the other jealous. Meanwhile, Carl makes a long overdue visit to a doctor, played by Star Jones Reynolds, who makes him think he has more ailments than he really does

To complete the GNB Management Training Program, Claude and Kipp must supervise a department. Claude is assigned to Supplies, where she struggles to assert her authority over hypersensitive Owen. Meanwhile Kipp is assigned to Operations, which he soon learns is the janitorial department. At first appalled at blue collar life, Kipp later embraces his new masculine side. Lydia fills in as Jeb's secretary, which proves awkward since they've broken up. Carl recieves 18 health code violations in the cafeteria, but the inspector agrees to wave them if he'll sleep with her.

Claude encourages Charlie to audition for a band, but she's dumbfounded when he reveals he got the gig and has to leave town indefinitely. Will wins Kipp from Jeb in a card game and gives him to Claude as a gift -- so Claude willingly lets him do her job. Meanwhile, Ramona and Owen plan a surprise birthday party for Carl. Depressed over her breakup with Jeb, Lydia (""the spinster Weston"") becomes Owen's ""pancake whore,"" but Claude interferes and Lydia winds up having an impromptu wedding with Jeb at Denny's.