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 her 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.
Claude is shocked, but elated, when Will asks her to dinner. Lydia is jealous at first, but when the "date" doesn't go as Claude had hoped, she and Lydia bond over ice cream. Meanwhile, Owen tries to enforce his office supply rules when he sees Kipp with a special executive-level pen.
Claude discovers that lying is part of her job description, and gets unsolicited training from Kipp. Meanwhile, at a companywide meeting, Lydia & Owen and Kipp & Ramona are paired up as 'floor buddies,' a program designed to help employees bond with one another — but can these incompatible groups ever really connect?
Claude is showered with gifts as Will's new assistant, leaving Kipp and Lydia filled with envy. Kipp deceives Claude by telling her that Will is not fond of her lowly 4th floor buddies, Owen and Ramona, and then Claude inadvertently offends them by saying they cannot visit her on the 22nd floor anymore.
Claude loves her job so much she doesn't want to use her vacation days. After reluctantly agreeing to take a vacation, she feels threatened by Luke, the popular temp who fills in for her.
Claude is unable to compete with Lydia for Will's attention, so Ramona drags her to a Strippercize class to help her gain confidence. Meanwhile, Kipp is unhappy with his I.D. photo and convinces Owen to return to his former job as an I.D. photographer.
Claude sees her future self personified by a bitter, hardened assistant named Roz, and she's afraid she'll end up the same way if she doesn't get a life outside of the office.
Claude's caught in the middle when her well-meaning but overprotective parents come for a visit and Will backs out of a dinner engagement with them. Meanwhile, Kipp begins losing his edge at work when he becomes smitten with a journalism student.
For the first time in her life, Claude is dating two men at once, one of whom happens to be Will's godson, Oliver (played by Aaron Buerge, better known as "The Bachelor," making his acting debut).
Claude discovers that the office holiday party is not the best place to give her boss relationship advice. But the night is not a total bust, as Claude, Lydia and Owen each make a special connection at the party.
Claude helps Kipp realize his dream of becoming a news anchor by producing a demo tape for him. Meanwhile, Lydia tries to jog Will's memory of their one-night-stand, but maybe she's the one with the bad memory.
Claude and Charlie are secretly dating, but they find it's a challenge to keep it hush-hush. Meanwhile, Lydia finds a mentor who turns out to need some mentoring herself.
While housesitting for Will, Claude has her friends over to his fabulous New York apartment. When Kipp comes over uninvited, he gets quite a shock when he discovers who is on Will's speed dial list.
Will's new girlfriend, Dani (Jenny McCarthy), enlists Claude to be her errand girl, while Lydia and Kipp buddy up to Owen to get into the VIP room of the hottest nightclub in town.
Claude has a spicy phone call with her boyfriend and is mortified when she discovers that Will has overheard them. Meanwhile, Owen is pursued by a baby-crazy woman who wants Owen as a sperm donor.
Claude is feeling down since she broke up with Charlie, but she feels even worse when she accompanies Will's fiancée to a bridal salon where they run into Trista (better known as The Bachelorotte), so her friends organize an impromptu slumber party to lift her spirits.
Claude decides to throw a grown-up cocktail party to celebrate her two years in New York, but the party takes a turn for the worse when Will arrives and grabs center stage.
With Will's contract up for renewal, Claude recruits Ramona, Lydia, Kipp and Owen to implement a plan to keep him from being replaced by the hot-shot London bureau chief.
Owen learns that he has successfully impregnated Deirdre, the office supply rep who was looking for a sperm donor. But he has doubts about his ability to be a parent, until Claude and Ramona find his own biological father, Max, and they meet for the first time.
Claude is caught in the middle when her charming older brother goes on a date with Lydia.
Will is asked to host a benefit dinner and chooses a squirrel clinic as the charity, which makes Claude's job of selling tables to the event a difficult one. Meanwhile, Carl gets Owen hooked on gambling and in trouble with a bookie.
On the season finale, a new Executive Producer, Ted Elliot, is brought in to GNB to shake things up, and Claude believes she can stay above the fray. She is shocked to learn, however, that not even Will can protect her from Ted's new way of business. For the first time, Claude is forced to question her future working for Will.
In the season premiere episode, Claude must decide if she's going to continue to work for famous anchorman Will Butler or accept the incredible opportunity to work for the new executive producer, Ted Elliott. When Will encourages her to go for the new position, Claude accepts and Kipp steps in as Will's temporary assistant — but will it work out?
After Claude sends Carl's resume down to Human Resources, she is stunned to learn that her influence gets Carl hired on the spot as the new cafeteria manager at GNB. Meanwhile, Kipp entertains an older woman who promises to help his career, but he later realizes she wants more than he bargained for.
Claude's apartment is robbed, making her question her choice to ever move to New York City. She begins to enlist the help of Owen, Ramona and Carl in organizing a community watch program in her building, but soon discovers that she's already more of a New Yorker than she thought, as now she just wants to be left alone. Meanwhile Jeb Denton, the arrogant, new on-air political pundit, joins the team and creates sparks with Lydia.
Claude decides its time for her and her friends to experience a truly fabulous New York evening, so she uses one of Will's many party invitations to plan a big night out. However, the gang encounters a few distractions along the way. Kipp also uses one of Will's invites and finds himself on the guest list at a very bizarre party. Meanwhile Lydia and Jeb decide that, despite having nothing in common, they are still attracted to one another.
After updating her career success on a high school classmate's web site, Claude reconnects with a crush from school and sparks fly. Meanwhile Kipp and Lydia fight over an expensive shampoo, and Carl bullies people into using his cafeteria suggestion box.
While following the strict rules of dating, Claude forces herself to wait before calling a cute guy she has met and ends up losing his number. But her luck may change when she stumbles upon another great guy at a Halloween party. Meanwhile Kipp and Lydia have a new plan to get themselves promoted, and it involves rare and illegal cheese.
Ramona is on guard when Vicki Devorski (Pamela Anderson), a former temp who stole her boyfriend, comes back to the office. Ramona jealously guards her current boyfriend so Vicki doesn't get her hooks into him. But when Ramona begins to neglect her friends, Vicki tries to make Claude her new best friend, all in an attempt to get at Ramona. Meanwhile, Owen and Carl discover their mutual obsession with catfights and hope to witness one in person.
Claude and Lydia get stuck rooming together when they travel to the White House Correspondents Dinner in Washington, DC. 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 asks Carl to move into their shared office space.
Owen's two moms come to town and join the gang at Claude's first Thanksgiving dinner in New York. Owen is forced to "come out" to his shocked moms, revealing that he is, in fact, straight, not gay. Meanwhile Kipp and Lydia are invited to Will's exclusive Thanksgiving brunch.
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.
Will tells Claude to fire his interior decorator, Toni, but Claude doesn't feel up to the task and enlists Ramona to help. Meanwhile, Owen and Carl disclose to each other that their fantasy girlfriend is Lydia — and their dream scenarios may become a reality.
Claude takes on the task of personally shopping for all of Will's Christmas presents for staff and for his girlfriend, Dani. But it all starts to go wrong when Claude accidentally gives the very expensive gift meant for Dani to Lydia — which makes Jeb very jealous.
Claude is excited when Will asks her to write a public service announcement that will clean up his tarnished image, but she's surprised to discover that Lydia is writing one as well. Meanwhile, Owen and Carl discover the VIP men's washroom at GNB and run into Good Morning America weatherman Tony Perkins.
Claude and Kipp engage themselves in a war of words over whose boss is better, Will or Jeb, which leads to a few silly misunderstandings. Carl turns up the heat on Owen and Ramona by providing them with a new thermostat.
Claude works up the courage to ask Mitch, a sophisticated new producer, out on a date. Mitch accepts, but things go awry when Claude has a little too much to drink. Meanwhile Will tries to use Bill Walton to intimidate Carl into trading one of his prized players on his fantasy basketball team, and Lydia and Jeb both use Kipp to find out if they are now dating exclusively.
Jeb's teenage son, George, is in town and Jeb wants him and Lydia to bond. But since Lydia is not good with children, she enlists Claude's help. Claude assists George with his homework project, which leads to him falling in love with her. Meanwhile, Owen, Ramona and Carl have a plan to grow tomatoes on a plot of land just outside Jeb's office, but they'll have to get past Kipp first.
Kipp's mother, Diane, pays an unexpected visit to GNB to see former flame Will Butler, which prompts a reunion between mother and son. Claude invites her new boyfriend, Mitch, over to her house for a romantic dinner, but Owen and Ramona suggest that she class her place up a little before he arrives.
Claude's boyfriend uses his influence to have Lydia moved to another floor. Claude is thrilled until she learns that Lydia is now working on the fourth floor with Owen and Ramona, and things are not going well. Jeb enjoys Lydia's absence and he and Kipp do some male bonding. Meanwhile, the cafeteria is converted into a blood donation center and Carl is mesmerized by a beautiful nurse who tricks him into donating blood.
Claude accidentally wrecks Carl's beloved car when she drives Ramona and Owen to their favorite lunch spot. Carl is further upset when he learns that Claude lied about why she needed to borrow the car in the first place, but will he forgive her? Meanwhile, Jeb hires Kipp as his assistant, but Lydia is afraid that Kipp will reveal her personal secrets.
Human resources executive Schmidtline (French Stewart) institutes a ban on office dating, which makes Claude and Mitch (William Ragsdale) question whether they can date and work together.
Claude takes over as editor of the office newsletter and enlists her co-workers as staff writers. Owen's first assignment as food critic is to review Eddie the sandwich guy (Jim Belushi), one of Carl's competitors. Kipp takes on the gossip column, while Lydia probes him for info on Jeb. And Claude betrays Will's trust when she shares with Ramona the secret tapes from his Canadian soap opera days.
Claude's best friend, Roxanne (Tori Spelling), comes to town for a visit and decides she wants to move to New York. Will ends up hiring her as his personal assistant, but Roxanne's lack of attention to detail causes her to screw up Will's important John McEnroe interview, leaving Claude to complete the interview on her own. Meanwhile, Carl and Owen play a trick on Kipp that leads Jeb and Lydia to think Kipp's losing his mind.
Claude is upset after her break-up with Mitch, so Owen decides to cheer her up with a game of "Pimp Hat," where everyone must draw a name from a hat and fix that person up. Claude directs all her romantic energy to finding Owen the perfect girl, while Carl, Kipp and Ramona each have memorable first dates.
In an effort to get rid of Lydia, Claude helps Jeb realize it's time to propose to Lydia so she can quit her job and stay home. Jeb agrees and enlists Claude's help in setting up a romantic night for the perfect proposal. He also assigns Kipp the task of gathering some guys to hang out with for his final hurrah after the proposal, but all Kipp manages to find are Owen & Carl.
Will is jealous of the publicity other network anchors are getting for their pro-social work, so he asks Claude to suggest a policy that can get him some positive press. Claude suggests helping the environment by adopting the "paperless office," but fails to consider how the new policy will affect Owen -- head of office supplies. Meanwhile, Kipp and Carl lose the key to Will's expensive car down an elevator shaft and must journey to the depths of the building to find it.
After Caleb (Will Friedle), a co-worker that Claude's dating, tells her he's not ready for a relationship, the very next day she and Ramona see him with another woman. Claude decides to confront Caleb to find out exactly what he didn't like about her. Meanwhile, Owen and Carl befriend Jeb by sharing with him their new hobby, the Roll-O board. And Will, who has started wearing an earring to get more publicity, has his interview with a journalist (Giuliana Depandi) interrupted by Claude's emotional crisis about her dating life.
Claude plays matchmaker between Ramona and the new office hunk, Mike (Erik Palladino), but unwittingly arouses Mike's interest in her. Meanwhile Jeb and Lydia skip out on work to handle affairs that not even Kipp may know about, while Carl has notions of becoming a secret agent and, along with Kipp, puts his "spy skills" to use to uncover the truth about Jeb and Lydia's activities.
Lydia, obsessed with planning her wedding, is driving her fianci, Jeb, crazy. Jeb decides to pay Claude to listen to Lydia discuss the wedding details so he doesn't have to, but complications result when Lydia begins to think of Claude as a real friend. Meanwhile, it turns out that the publicist assigned to promote Will's new biography, Tracy (Lucy Lawless), is an old flame, and they rekindle their romance. And Owen and Carl find that communicating through walkie talkies allows them to be more candid with each other.
Ramona and Claude stumble upon an aged co-worker who has passed on to the next world, and when no one claims his belongings, Claude resolves to find his next of kin. Ramona, for her part, seizes the opportunity to move into the former colleague's office after finding out that Lydia wants to store her wedding materials in it. But a spirit seems to haunt the office, frightening Ramona and Owen and climaxing with supernatural events on Halloween Night. Meanwhile Carl, decked out as a Musketeer, flirts with a cafeteria patron dressed as a genie... will they reveal their true selves? And will Lydia and Jeb really go to the company Halloween party as Franklin and Eleanor Roosevelt? Find out when the GNB staff celebrates Halloween in elaborate costumes.
Will, upset about an on-air blunder during his news broadcast, blames his mistake on his faulty anchor chair. Claude has the chair checked out, learns there's nothing wrong with it, and tells him so. When Will continues to insist the chair was the problem, Claude calls him a diva. Hurt by the comment, Will sends Claude to see his therapist. Meanwhile Lydia sees Will's on-air slip as an opportunity for Jeb to step into the anchor position, and Kipp breaks up with his girlfriend, Annie, but is scared into reuniting with her after he finds a gun in her purse.
Claude applies for the GNB Management Training Program, assured by Ramona that she is a "shoo-in" to be selected. But when Kipp also applies for the program, it remains to be seen what will be Claude's greater obstacle to acceptance, Kipp or her own blossoming confidence. Meanwhile, Jeb learns Lydia plans to stop working once they're married, so he enlists Kipp to convince her otherwise -- but Jeb should be careful what he wishes for; and Owen and Carl conspire to make big money supplying fish to the GNB cafeteria, but their plan is endangered when Ramona becomes suspicious.
When Claude and Ramona suspect Kipp is bankrolling his Lasik surgery with ill-gotten company money, they go undercover to learn the truth. Meanwhile, Lydia is shocked to learn Jeb is hiding a dirty little secret about the fancy hotel she's chosen for their romantic rendezvous, and Owen and Carl help Will train for the NYC Marathon.
It's the day after Thanksgiving and Owen's two moms visit GNB to meet his coworkers. Judy (Joanna Kerns) helps Will with his girlfriend problems and Judith (Valerie Harper) lives vicariously through Carl and Ramona, encouraging them to indulge in her passions for gambling and drinking. Meanwhile, Claude fears losing her job when Owen reveals that she's secretly interviewing for another job, and Lydia's first Thanksgiving with Jeb's family does not go well when his grandmother kicks the bucket under mysterious circumstances.
When Claude learns Carl's next "romantic" date with Vivian will consist of taking her out for 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, 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. Meanwhile, Will and Jeb are left to fend for themselves in the office.
Claude's ex-boyfriend, Charlie, returns to GNB and they decide to give their relationship a second try. Ramona convinces Claude to buy some sexy lingerie to reignite their passion, and Claude finally feels confident enough in her own skin to wear it, but is later embarrased when she is strip-searched at work. Meanwhile, GNB has 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 when he makes a terrible mistake, Lydia jumps in to help her friend.
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.
Claude is excited to be starting the GNB Management Training Program with her new boyfriend, Charlie - until Kipp joins the program and befriends Charlie. Meanwhile, Owen volunteers to photograph Lydia and Jeb's wedding, but Lydia is uninterested until she sees his work up at a prominent New York art gallery. Paula Abdul guest stars as Kathleen, Will Butler's girlfriend and art gallery owner.
Will gives Claude the keys to his home in the Hamptons for a romantic weekend with Charlie, but when they arrive they're surprised to find that Lydia and Jeb had the same idea. Meanwhile Ramona makes a romantic connection with the geeky computer technician, Morpheus (Mark Curry), Carl and Kipp compete for the affection of the beautiful yet unattainable new producer, Laura (Kimberly Williams-Paisley), and Will gets a private lesson in his office from his tai chi instructor, Xin Xao Pi -- hilariously played by Regis Philbin.
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 designers Tracy Hutson, Michael Moloney and Paul DiMeo (guest starring as themselves) redesign the apartment, Claude has to spend the night at GNB -- where there is a surprising amount of late night activity and intrigue.
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.
Claude encourages Charlie to audition for a band, but then, when he makes the cut and has to leave town indefinitely, she realizes her relationship skills are better applied to Jeb and Lydia. Meanwhile, Owen and Ramona throw a surprise birthday party for Carl, but it turns out to be a much bigger celebration than they'd expected.
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 that difficult. Meanwhile, Jeb incites a power struggle between Lydia and Kipp to keep them both distracted and out of his hair.
Claude reveals to Ramona that she and Carl are sleeping together and asks that she keep it a secret from Owen. Owen then senses that something is going on, so he asks Carl, who reveals nothing. But later that night, Owen pays Carl a visit and ends up walking in on Claude and Carl having sex. Meawhile, Jeb & Lydia are constantly fighting at work, and Kipp loses his trust fund and looks to Ramona to help him budget his money.
Flirting with De-feet Claude is concerned when Carl doesnt seem to be affected by her flirting with Ethan, 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 attempts to protect the owls living on her apartment building's roof. Meanwhile, Owen desperately searches for someone to be his emergency contact.
When Jed is described as boring, Claude decides to get him publicity, but accidently ends up getting it herself.
When Kip loses his apartment, Carl decides to take him in. Kip then gives Carl advice on how to date Claude, he reveals he knows a lot more about her than he thought.
Owen helps Claude deal with a moody Lydia, Kip finds out that Jeb picks on him because he is a weak target, and are Ramona and Carl related?
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.
Ramona and Owen are forced to eat in their office when they are banned from eating on the 22nd floor.
In the last ever episode Claude realises that Lydia is about to cheat on Jeb after hearing a phone call, but later wishes she had stayed out of it.