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Claude Casey moved up in the secretarial world of television news, from temp to the anchor's desk. After her boss hires her full time, Claude realizes she may be in over her head in this world of assistants fighting to get ahead. But Claude is determined to prove that though she may not be perfect, she's not going down without a fight.
Sara Rue
Claude Casey
Sherri Shepherd
Ramona Platt
Andrea Parker
Lydia Weston
Zachary Levi
Kipp Steadman
Patrick Warburton
Jeb Denton
Andy Dick
Owen Kronsky
Will Sasso
Carl Monari
2006
Upon returning from vacation, Claude learns that her boss, network anchor Will Butler, has resigned, leaving her jobless. Luckily her trusty friends, Owen and Ramona, have secured her a position as a temp on the 4th floor, right back where she started three years ago. Jeb Denton, the new anchorman, has promoted his wife, Lydia, to producer, and Claude's worst nightmare comes true when she's offered a job as Lydia's assistant. She hesitantly accepts the job on condition that she be given more responsibility, but working for Lydia proves to be a dangerous bargain. Meanwhile, Owen becomes addicted to Carl's new soft serve ice cream machine.
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.
After a long week, Claude, Carl, Ramona and Owen enjoy a night out for happy hour at their favorite bar. A little tipsy, Claude and Carl head home and, when one thing leads to another, they end up in bed together. They decide to keep it a secret from everyone at work to protect their friendship, but their attraction to each other makes it difficult. Meanwhile, Jeb incites a power struggle between Lydia and Kipp to keep them both
Claude reveals to Ramona that she and Carl are having sex with each other. Unfortunatley, Owen also finds out about this on his own.
Claude is concerned when Carl doesn't seem to be affected by her flirting with Ethan (Joey McIntyre), the copy repairman. Meanwhile, Ramona finds out that Kipp is making money on the side as a foot model, and she demands to get involved. Owen takes the photos of their feet together, but when they find them online, it turns out that someone has turned their shoot into a bizarre sexual scene.
Claude has owls living on her apartment roof and does her best to protect them, but gets distracted by Lydias dog, who ends up scaring them away. Meanwhile Owen tries to get someone to be his emergency contact, but no one wants the responsibility since he's so accident prone.
Claude brings Jeb to a hip magazine party with the intention of raising Jeb's profile; Owen and Ramona start a protest at the cafeteria.
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.
Claude realizes that part of her job is predicting Lydia's mood swings and Owen gives her a tool to do it.
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 and Kip get into an argument when she is about to become assistant to Lydia and Jeb.
Claude makes an announcement; the fourth floor workers are banned from the snack bar; Ramona and Owen are forced to eat in their office.
Claude intervenes when she realizes that Lydia is about to cheat on Jeb. Meanwhile, Owen plans to seduce Lydia, and Jeb loses his voice.
2003
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."
2004
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.
When Will makes an on-air flub, he attributes it to a wobbly chair and refuses to do the news again until the chair is fixed to his liking. Claude innocently calls him ""a diva"" and suffers Will's wrath: an hour on his psychiatrist's couch. Meanwhile, Lydia schemes to get Jeb on the air in Will's absence; Owen develops an obsession with bubble-wrap; Carl focuses his anger on Ramona when they add a self-checkout to the cafeteria; and Kipp fears that he will literally be shot by the girl who he just broke up with.
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.
2002
Claude's dream comes true when she moves up from temp to a permanent position as the assistant to news anchor Will Butler. But all is not quite as she had imagined when she realizes that new co-workers Kipp and Lydia will stop at nothing to sabotage her. Meanwhile Claude's trusty friends Ramona and Owen begrudgingly help her transition from the comfort and safety of the fourth floor to the battlefield that is the 22nd floor, while Claude tries to hide her crush on Will Butler, who is just less than perfect.
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 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.
Feeling jealous over Claude being showered by gifts for being Will Butler's assistant, Kipp and Lydia try to break Claude, Ramona and Owen's friendship. Kipp tells Claude that Will doesn't like her having her 4th floor friends around his office, which Claude believes. She politely asks them to stay on their floor, which they take offensively. Now Claude feels bad for sending her friends away, and tries to work her way back into their friendship circle. Meanwhile, Lydia struggles with her (lack of) good sense after she feels guilty for switching Ramona's original Prada hangbag for a cheap imitation. She was trying o save the purse from being ""killed"" by Ramona's exquisite fashion taste and personal alterations on the wonderful Italian leather.
Ramona tells Claude she has to use her vacation days in the next few days or else she'll lose them. Claude refuses to leave Will even for a week, and Ramona (trying to be a good friend and give Claude a break from her overbearing work) sends a memo to Will about Claude's vacation. Forced to take a break, Claude pretends to go to Niagra Falls and sneaks around the office when she meets her temporary replacement – who she thinks might take her job. Ultimately, Will reassures her she doesn't have to worry about her job; he wouldn't trade her for the world. As for Kipp's dream job of becoming an associate producer, well, that will have to wait a little longer. Torturing Claude with lies about Luke's resume might have given Luke a promotion he never expected in such short notice.
Tired of living in constant competition with Lydia over Will's attention, Claude decides to attend Ramona's ""strippercize"" class to develop her ""uh-uh"". Claude quickly gains the self-confidence that she's been lacking, so she and Ramona go out for drinks, where Claude finds herself competing for men -- against Lydia. Meanwhile, Kipp asks for Owen to help him take a good picture for his id card, and Owen obliges... but Kipp soon discovers that Owen is too much of a perfectionist.
Claude accidentally starts a feud with Roz, the company's president's secretary, but being the good hearted girl that she is she wastes no time on trying her best to make up with Roz. Roz sees in Claude a younger version of herself and tells Claude that will be her in 30 years, and Claude freaks out about it after realizing that indeed she has no personal life outside the workplace. She joins a pottery class and tries to make a gravy boat that ends up looking like a squirrel. Lastly, she tells Will she loves working for him, but doesn't want to be stuck as a secretary all her life. Will assures her she's very talented and can be anything she wants. Meanwhile, Kipp buys a 1500 dollar Armani suit and Owen thinks he bought it from him for a hundred bucks after he lent it to Kipp. When Owen doesn't hold the elevator door for Roz, she prepares her revenge. When Kipp shows up for an interview with the company president, Roz retaliates on him, thinking he was the one to leave her waiting in t
Claude's parents are visiting her at the office, and can't wait to meet famous anchorman Will Butler. They invite him to join them for dinner and Will says ""that would be great"", leading the Caseys to think he will show up, when in fact he won't since """"that would be great"" means ""ain't gonna happen"". Claude doesn't know how to break the news to her parents, and takes the blame for it. They are disappointed at Will, and embarrass Claude by giving him a lecture when he decides to surprise Claude and show up unexpectedly. Meanwhile, Kipp is idolized by a college student and falls for her, only to get his heart broken after she gets a job as associate producer at CNN and he is left alone with his lies.
Claude scores a date with Charlie from travel after accidentally throwing her hair on his face. They have a wonderful time together, and the next morning Claude is ecstatic about it. Will introduces her his godson Oliver, and asks Claude to show him around town. He asks her out on a date, and ends up accepting to go out with him after Will pressures her to. Claude tries to jiggle dating two men, but her scheme soon falls apart when Will comments on her date with Oliver in front of Charlie, who leaves heartbroken. Claude feels bad gets advice from Ramona and Lydia on how to dump Oliver and get back with Charlie. Meanwhile, Kipp starts sucking up to Mr. Turnbach's son hoping for a chance of a promotion.
It's time for the Christmas party, and Claude keeps hanging around Will, making sure he's got everything just the way he wants. When he tells her to loosen up a bit and act casual because she's not on the clock, Claude gets a little too personal and talks about Will's personal life. She spends the rest of the party worrying about the impression she gave and tries to make up for it, but only make things worse when she accidentally tells Will she had a crush on him. Meanwhile, Kipp keeps trying to find some big-shot producer who will promote him, and after a number of unsuccessful attempts he announces on the mic he's quitting. Ramona is a big success with her enormous cleavage and Owen and Lydia end up making out after both have a lousy time at the party. The next morning, Kipp tells Claude nothing that happens on the Christmas party counts, and she thinks twice about the cute guy she met on the bar.
Kipp broke Claude's penguin toy, but instead of planning a meaningful revenge against him, Claude decides to help him make a demo tape on which he can show his news anchor abilities and she can show her producer skills. Of course, Kipp's attitude on the newsset it completely corky, which ends up as a very funny – and very humiliating – demo tape. But Claude is too good hearted to let Kipp go through that kind of embarrassment in front of everyone and decides to destroy the tape (and Kipp's trust on her). Meanwhile, Lydia tries to prove that Will hasn't forgotten about their night together and ends up realizing she is the one who forgot about it.
Ramona and Owen wonder why Charlie and Claude stopped seeing each other, while they have been secretly dating, trying to keep a low profile on a inner-office relationship. But that is no easy task since Ramona and Owen seem to be all over the place. Claude talks Charlie into telling their friends, which he agrees on since she trusts them so much. The next day everyone in the building knows about it, which makes them very uncomfortable. The solution? Go back to how things were. They break up in public and go back to their little secret affair. Meanwhile, Lydia asks big shot Norma Craft to be her mentor, but ends up being the listener to all her personal problems. Seeing that her scheme is taking her nowhere she hoped it would, she decides to pull the plug on it – just in time, as Norma was planning to set cat's poop on fire on Alan Turnbach's table!
Will leaves his apartment to be taken care by Claude while he's gone, and tells her she can bring whoever she wants to it. She quickly organizes a small party just for her closest friends, which does not include Kipp, who stole her idea for a story. Lydia gets obsessed in finding a crystal gazelle she gave to Will and after she does she spends the whole evening trying to rescue it from the fish tank. Kipp drops by unannounced and discovers by accident that Will has his mom's phone number on his speed dial. Turns out his mother and Will have been sleeping together for a good time now, which causes a lot of awkwardness on both parties, and it's up to Claude to fix things.
Will's got a new girlfriend, Dani, who insists on having Claude run errands for her. Ramona and Owen convince Claude to put her feet down and stop being a pushover for Dani. When she finally confronts Will's new girlfriend, she imposes him to choose between her and Claude. Although happy to see Dani out of her life, Claude has to put aside the pride and talk her into getting back together with Will, who's been miserable without her. Meanwhile, Lydia and Kipp start sucking up to Ramona and Owen when they find out they have access to the VIP area at an important party.
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.
In celebration of two years in NY, Claude decides to throw a party at her place. But when Will says he'll go (a direct result from his publicist's attempt to popularize his image), she changes her party from casual to fancy. The only thing she wasn't counting on was Will showing up in casual clothes and turning her party into exactly what she wanted to avoid. In the end Ramona questions Claude about the reasons of her sadness and shows her that even though her party might not be the fanciest people sure are having fun.
Will's contract is up for renewal just as the head of the network arrives, flaunting a new anchor. Fearing that Will's job is in jeopardy and they'll be replaced, the staff bands together to pull of ""The Gum Caper"" to ensure Will a new contract.
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's brother shows up for a visit and Lydia is quickly interested in him. While the thought of the two dating disturbs Claude at first, she comes to terms with it once she sees how happy (and nicer) is makes Lydia. But she accidentally tells her brother that Lydia is crazy about him, and he decides to dump her. Lydia is devastated and it's up to Claude to clear things out. Meanwhile, Owen states on the inner-office magazine that he beats Will on chess all the time and Will comes down to challenge him.
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.
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...
