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'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.

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.

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.

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.

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.

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.

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.

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 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'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.

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.

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.

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.

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.

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).

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.

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.

Will hires Claude's old firend Roxanne Fiedler(Tori Spelling), 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.

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.

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.

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!

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 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.