At Will's urging, Claude takes a job as Mr. Elliot's assistant, leaving her position to be filled by Kipp -- who Will can't stand. Meanwhile, Lydia unsuccessfully tries to impress Mr. Elliot; Ramona and Owen fight over a lunchroom meal plan; and Carl hangs around the office because he locked himself out of his apartment.

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.

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.

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 uses her high school's website to hook up with a down-on-his-luck former classmate and the sparks instantly fly -- until Claude discovers that he's better off than she realized. Meanwhile, Kipp and Lydia fight to get a $100 bottle of shampoo, and Carl gets his feelings hurt when he implements a suggestion box in the cafeteria.

Claude meets a man in the elevator, but refuses to give him her number, so she takes his instead. She is trying out some new dating rules and decides not to call him until the initial 48 hours are over. There's a Halloween party coming up and Claude decides to take Trevor, but unfortunately his number was in the pocket of the jacket she traded in for a party dress. They track down the new owner, but he washed away Trevor's number. Despite her lack of luck, she manages to meet another guy at the party. Meanwhile, Kipp and Lydia smuggle an illegal cheese in order to impress their superiors and earn promotions, but the cheese is eaten by Ramona, Owen and Carl.

When Vicki Devorski, a former temp who once stole Ramona's boyfriend, comes back to the office, Ramona jealously guards her current boyfriend. But when Ramona begins to neglect her friends, Vicki tries to make them her new best friends. Meanwhile, Carl and Owen discover their mutual obsession with catfights, and Kipp gets stuck throwing a birthday party for Lydia.

When they travel to the White House Correspondents Dinner in Washington, DC., Claude and Lydia get stuck rooming together with an uninvited Kipp. Lydia has a lot of advice for Claude on how to conduct herself in the nation's capital, but everything changes when Lydia runs into a childhood friend who exposes her middle class background. Meanwhile, Ramona gets upset when Owen blows her off to hang out with Carl, but the situation worsens when Owen invites Carl to share their office.

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.

After Carl asks Claude out for a spontaneous dinner, the office rumor mill kicks into gear, until Claude has a talk with him about where their relationship is going. Meanwhile Lydia's outrageous spending habits get her into financial trouble, so she enlists Ramona as her financial advisor(ABC).

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.

Claude takes on the task of personally shopping for all of Will's Christmas presents for staff and later for his girlfriend, Dani. Her efforts start to go awry when Lydia and Dani's gifts get switched, making Jeb jealous and offending Dani.

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.

When Kipp stirs up a competition with Claude over whether Jeb is a better boss than Will, it escalates until Kipp discovers that Jeb's job is in jeopardy. Meanwhile, Carl gets a thermostat installed in Owen and Ramona's office, which Ramona demands that Owen keeps set on high heat.... leading Owen and Carl to hatch a revenge scheme that goes awry.

Claude sets her sights on Mitch, the new segment producer. In preparation for their date, Claude starves herself to get into a dress, but problems arise when they get to the restaraunt and her drink instantly kicks in. Meanwhile, Will goes to great lengths to get Carl to trade Shaq to him in the office ""fantasy basketball game,"" and Jeb and Lydia each try to determine if they are an exclusive couple.

Lydia agrees to watch Jeb's son, George, when he comes for a visit, but she quickly pawns him off on Claude. But when George develops a raging crush on Claude, Lydia fears that it will hurt her standing with Jeb. Meanwhile, Ramona finally recieves her grandmother's prized tomato seeds from probate and schemes with Owen and Carl to plant them outside of Jeb's office -- but they have to contend with Kipp.

Claude invites Mitch to her apartment for some dinner and romance, but her friends convince her that her décor is a bit childish. Kipp's mother, Diane steps into town to meet Will Butler for a fling of her own, and swipes one of Claude's childhood drawings to pass off as Kipp's. Meanwhile, Owen gets a motorscooter, Ramona gets tickets to a Mary J. Blige concert and Lydia makes spa reservations for herself in Diane's name.

Mitch uses his power to bump Lydia off the 22nd floor to make Claude happy. Even though Lydia's transfer has made life on the 22nd floor serene, Claude tries to bring her back from the 4th floor to ease Owen and Ramon's suffering. Meanwhile, Carl is angered that they're using his cafeteria to hold a blood drive, but he changes his tune when he meets a gorgeous nurse.

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.

When Mr. Schmidtline holds a ""Respect in the Workplace"" seminar and cracks down on office romance, Claude fears for her relationship with Mitch... so she sets up Ramona with Schmidtline. Meanwhile, Jeb recruits Carl as a soundman to capture a taped confession from Lydia that he didn't coerce her into their relationship. Kipp calls Owen ""four eyes,"" which he should come to regret when he loses a contact and is caught wearing glasses -- but Owen can't muster a clever remark.

As Claude takes over editing the company newsletter due to the death of the previous one, she hires Owen to write a review comapring Carl to Eddie Smirkoff, the new sandwich guy. Meanwhile Will Butler orders her to destroy videotapes that she thinks are old pornography, but turn out to be evidence of his early career as an actor on a Canadian soap opera.

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 is heartbroken when Mitch goes on assignment to Budapest, so Owen and Carl try to lift her spirits with a game of "Pimp Hat," where everyone picks a name out of a hat and sets up a date for them. Kipp joins in the game, secretly plotting to ruin everyone's evening, and Lydia becomes jealous that she and Jeb don't have a good "first date story."

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."