When Mitch leaves for Budapest, it leaves Claude heartbroken. To help her, Owen and Carl organize a game of "Pimp Hat." Kipp joins in the game planning to ruin everyone's evening. Lydia is envious that she and Jeb don't have a good "first date story."

Claude prods Jeb to wed Lydia. Claudia believes it will ensure Lydia remained at home and not cause her problems. Jeb, meanwhile, instructs Kipp to recruit guests for a "man party."

Despite being unqualified for the job, Will hires Roxanne Fiedler as secretary, Claude's old friend. Meanwhile, Kipp is assumed to be going crzy thanks to pranks by Carl, Owen and Ramona.

When Claude decides to handle the responsibility of editing company newsletter, she asks Owen to write a review comparing Carl to Eddie Smirkoff, the sandwich guy. Will Butler orders destroying videotapes which she believes is pornography. The tapes later turn out to be footage of his performance on a Canadian soap opera.

Claude fears for her relationship with Mitch when Mr Schmidtline holds a "Respect in the Workplace" seminar and forbids office romance. Claude sets up Ramona with Schmidtline hoping it would not create problems in her relationship. Jeb enlists Carl's help to capture on tape Lydia's confession that their relationship was consensual and not coerced by her.

To make Claude happy, Mitch ensures Lydia is shifted from the 22nd floor. Lydia's exit results in life becoming serene on the floor; however, Claude tries to bring her back to help ease Owen and Ramon's suffering. When Carl learns that his cafeteria would be the venue for a blood donation camp, he is fuming mad. However, his anger dissipates when he meets a gorgeous nurse.

Claude invites Mitch for a dinner date but gets second thoughts after her friends convince her that the decor of her house was childish. Lydia makes spa reservations in Diane's name, Owen gets a motorscooter and Ramona gets tickets to a Mary J Blige concert.

Jeb's son, George comes for a visit and Lydia agrees to watch him. However, she quickly dumps him on Claude. Lydia starts regretting her decision when George develops a crush on Claude and she fears it will affect her standing with Jeb. Ramona finally receives her grandmother's prized tomato seeds and plans to plant them outside Jeb's office along with Owen and Carl. However, the trio have to contend with Kipp.

Kipp is shocked on learning from Claude that Jeb's job is in jeopardy. Carl gets a thermostat installed in Owen and Ramona's office. Carl and Owen hatch revenge scheme after Ramona insists on setting the thermostat on high heat.

Will goes into damage control mode after an altercation with the paparazzi and enlists Claude to write a public service announcement. He hopes it will help clean his tarnished image. Claude is thrilled until she learns that Will had granted the opportunity to Lydia too.

Claude sets out with Ramona and Owen to find a better lunch on Carl's Buick Riviera. The quest ends when she wrecks the car. Lydia praises Kipp in front of Jeb who promotes Kipp to his assistant. However, Lydia fears Kipp will reveal unflattering secrets about her to Jeb.

Claude volunteers to shop for Will's Christmas presents for the staff and also for his girlfriend, Dani. Claude's efforts go awry when Lydia and Dani's gifts get changed, leaving Dani offended and Jeb fuming with jealousy.

When Will asks her to fire his interior decorator, Claude seeks Ramona's help. Kipp overhears Owen and Carl confessing their crush on Lydia and describe her as their fantasy girlfriend.

Claude decides to invite her friends for Thanksgiving. When Owen's two lesbian moms (Valerie Harper and Joanna Kerns) come visiting, it creates fresh problems for him as they believe him to be gay. Owen decides to keep up the ruse and asks his friends to play along. On Owen's request, Carl decides to pose as his lover. Lydia and Kidd, meanwhile, get invited to Will's Thanksgiving party. Kipp turns out to be the star attraction at the party.

Claude and Lydia are forced to share room with Kipp when they arrive at Washington, DC., for the White House correspondents dinner. Lydia tutors Claude on how to conduct herself in the US capital. Owen upsets Ramona when he decides to hang out with Carl instead of spending time with her.

When Carl invites Claude for dinner rumor mills go into overdrive… which in turn leaves Claude questioning his motives. Deep in debt, Lydia enlists Ramona as her financial advisor. Her move doesn't bode well with Kipp. Kaitlin, Will's niece, gets an intern job at GNB.

Claude gets the number of a stranger whom she met in the elevator. She decides to wait for 48 hours before calling him. However, her plans go kaput when she sells her jacket with the stranger's number in the pocket. Meanwhile, to impress their superiors, Kipp and Lydia buy illegal cheese.

Claude decides to take Ramona and Owen to a Vogue retrospective. However, the plan goes haywire due to Claude's last minute decision to invite Carl. Kipp prepares a list of his ideal mate's qualities which he forgets on Lydia's desk. It is later found by Jeb.

Vicki Devorski's return triggers alarm bells in Ramona. Having lost a boyfriend to Vicki, Ramona zealously shields her current boyfriend. In the bargain, Ramona starts neglecting her friends and Vicki tries to get close to them. Carl and Owen, meanwhile, discover their mutual obsession with catfights. Kipp gets stuck with organizing birthday party for Lydia.

When Carl's videostore shuts down, Claude submits his application at GNB. As she types his resume on stationery that reads, “From the Office of Will Butler,” his application is considered favorably and Carl receives a job as cafeteria manager. However, Claude develops fears that his performance will reflect badly on her. Kipp's plan to ascend the corporate ladder rebounds when his elderly target wants him to satisfy her sexual needs.

After Claude's flat is robbed, Owen and Ramona move in with her. Claudia channels her energies into making the building into a little community. Lydia, meanwhile, flirts with anchorman Jeb Dentor but her efforts come a cropper.

On Will's prodding, Claude agrees to work as Mr. Elliot's assistant which left her position to be filled by Kipp, whom Will can not suffer. Lydia, meanwhile, tries to impress Mr. Elliot but with little success. Differences over lunchroom meal plan results in a duel between Ramona and Owen. Having locked himself out of his apartment, Carl has no option but to hand around the office.

Sparks instantly fly when Claude hooks up with a former classmate using her school's website. To her shock and surprise, Claude realizes that the classmate, whom she believed to be down-on-his-luck, is better off than she realized. Kipp and Lydia fight to buy a bottle of shampoo worth $100. Carl's feelings are hurt when he implements a suggestion box in the cafeteria.