Claude finds an invitation for a Vogue retrospective at the Guggenheim museum in Will's junk mail and decides to take Ramona and Owen with her to a glamorous New York evening. But their plans hit a snag when Claude makes the last-minute decision to invite Carl. Meanwhile, Kipp makes a list of his ideal mate's qualities, which he leaves on Lydia's desk -- but Jeb finds it and assumes it's Lydia's.

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.

Claude's new sway jacket is ruined because someone stole her umbrella, forcing her to go out in the rain. When she returns to the building, however, she runs into the guy who stole it and confronts him, only to find out later that he's Ted Elliot, the new executive producer. With her job on jeopardy, Claude has a change of attitude, but Ted is such a jerk to everyone that she stands up for her morals. Impressed, Ted offers her a job as his assistant, leaving Claude with a dilemma: does she continue to work for her beloved Will Butler or does she dump him for a job with a much more promising future ahead of her? To be Continued...

Claude hawks tickets to Will's benefit dinner for a squirrel clinic, Owen gets in trouble with a bookie, and Kipp & Lydia scheme to get free merchandise.

Learning that Owen has ""sired"" a child, Claude tries to arrange a get-together between Owen and the dad he's never known. When ""braces guy"" gets a promotion, Kipp decides that he needs a gimmick to get noticed -- so he becomes ""bicycle guy."" A bad photo in the paper has Will feeling self-conscious about aging, so he recruits Lydia to make him over.

Claude sees herself struggling with her moral values when she is forced to lie for Will. She feels bad about covering up one of Will's escapades and lying to Ramona and his wife about it, but it's all good after Claude talks to Ramona. Meanwhile, the employees attend a companywide meeting where they have to pick a "floor buddy", someone from another floor for them to bond with. Lydia is at first annoyed by Owen but later misses him after she realizes he treated her like no one else did. And Ramona and Kipp pretend to dislike each other after having a great time in the Hamptons.

It's Valentine's Day and Lydia is feeling jealous of Claude over a dozen roses she got from Charlie, who's on a road trip with his father. The next morning, two dozen roses mysteriously appear on Lydia's desk, and she wonders who is her secret admirer. Claude finds out it's Kipp, but decides to keep it down because no one would believe that. Meanwhile, Claude has the most embarrassing moment of her life when Will overhears her talking dirty with Kipp on the phone; and Owen is seduced by a gorgeous girl who only wants his sperm to make a baby, leaving Claude and Ramona the mission of opening his eyes not to let a child grow without a father.

After breaking up with Charlie, Claude is feeling low. Will's fiance insists Claude accompany her to a bridal salon, which only serves to upset Claude further. They run into Trista Rehn (star of ABC's reality show, The Bachelorette), who got engaged on the show and is trying on wedding gowns. Claude locks herself in a dressing room to cry, wiping her nose on a wedding gown, and Trista trys to comfort her through the door. Claude's friends rally round, even Lidia, and try to cheer Claude with an impromptu slumber party and girl talk.

Claude's apartment is robbed and she decides to call a neighbor meeting and organize her building into a more friendly community. Her good intentions soon turn into an excuse for all neighbors to use her to run them errands. Finally Claude decides that the building doesn't have to function as a small town and stands up for her freedom, even if it means telling Ramona and Owen that she doesn't want them living there anymore. Meanwhile, Lydia has another unsuccessful attempt of flirting with a superior.

When Lydia feels she doesn't get enough recognition, Jeb and Claude come up with a plan to give her a fake award, but they soon get too over their heads when Lydia gets too excited about the award.

Claude nudges Jeb into marrying Lydia, so she'll stay home and be out of her hair for good. Meanwhile, Jeb instructs Kipp to recruit guests for a post-proposal "man party."

When Claude is unexpectedly asked out for dinner with Will, she quickly cancels her double-date plan with Ramona. But when the ""date"" turns out to be less of one than she anticipated, Claude finds solace in the company of Lydia -- who assumes that Claude slept with him. Meanwhile, Owen tries to assert authority over Kipp and the two feud over an expensive pen.

Claude makes an announcement; the fourth floor workers are banned from the snack bar; Ramona and Owen are forced to eat in their office.

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.

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.

When the videostore that Carl works for goes out of business, Claude agrees to turn in an application for him at GNB. She types his resume on stationary that reads, ""From the Office of Will Butler,"" so his application is rushed through and Carl recieves a job as the cafeteria manager -- but Claude fears his performance will reflect badly on her. Meanwhile, Kipp's plan to climb up the corporative pyramid backfires when his elderly target ends up wanting him for sexual purposes.

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.

After an altercation with the paparazzi, Will enlists Claude to write a public service announcement in hopes that it will clean up his tarnished image. Claude is ecstatic until she learns that he granted Lydia the opportunity to write one too. Meanwhile, Owen and Carl bask in the luxuries of the VIP men's washroom at GNB, but fellow tresspasser Kipp tries to keep them from invading his turf.

Claude is throwing her first Thanksgiving for all her friends. Owen's two lesbian moms (Valerie Harper and Joanna Kerns) come to visit and share the holiday. The only problem is that his moms have always assumed that Owen is gay. Hoping to keep up the ruse, Owen asks his friends to play along, including asking Carl to pose as his lover. Meanwhile, Lydia and Kipp both get invited to Will's Thanksgiving party, where Kipp is briefly the star attraction.

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.

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.

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.

During a transit strike, Claude borrows Carl's beloved Buick Riviera and sets out on a quest with Ramona and Owen to find a better lunch... a quest that promptly ends when Claude wrecks the car. Meanwhile Lydia talks up Kipp in front of Jeb, who promotes Kipp to his assistant -- but Lydia fears that Kipp will reveal unflattering secrets about her.

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.

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.

Will tells Claude to fire his interior decorator, but Claude doesn't feel up to the task so she enlists Ramona to help... but Ramona quickly becomes drunk with power and begins going beyond the call of duty to help out Claude. Meanwhile, Owen reveals to Carl that Lydia is his ""fantasy girlfriend,"" so Carl claims her too -- and Kipp overhears their conversation.

Will hires Claude's old friend Roxanne Fiedler, as a new secretary, even though she's totally unqualified for the job. Meanwhile Kipp is assumed to be going bonkers Gaslight-style, thanks to some pranks by Carl, Owen and Ramona.

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.

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

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.

After quitting as Lydia’s assistant, Claude is back to “floater” status. However, the only spot available is working with Lydia, so Claude reluctantly agrees to work for her, but with conditions. Lydia’s first major assignment is to produce a complicated segment for the news. She pretends to have everything under control, but ends up breaking down and begging Claude for her help. Claude saves her only after she’s given a raise, a promotion and an apology. Meanwhile, Ramona gets a call that she may need to quit and return to the National Guard, leaving Owen and Carl freaking out.

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.

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.

When Kip reveals he lost his apartment with his trust fund, an unwitting Carl takes him in. Kip then gives advice to Carl about dating Claude. Kip reveals, through their hatred, he knows a lot more about Claude then he thought. Ramona and Lydia listen to Claude talk about her and Carl's relationship. Meanwhile, Jeb receives a watch from Lydia that he hates. But in the hands of Owen, it's not safe.