Less than Perfect

Claudes 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 Claudes 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.

Claude sees herself struggling with her moral values when she is forced to lie for Will. She feels bad about covering up one of Wills escapades and lying to Ramona and his wife about it, but its 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.

Ramona tells Claude she has to use her vacation days in the next few days or else shell 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 Claudes 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 doesnt have to worry about her job; he wouldnt trade her for the world. As for Kipps dream job of becoming an associate producer, well, that will have to wait a little longer. Torturing Claude with lies about Lukes resume might have given Luke a promotion he never expected in such short notice.

Claude accidentally starts a feud with Roz, the companys presidents 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 doesnt want to be stuck as a secretary all her life. Will assures her shes 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 doesnt 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 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. Turnbachs son hoping for a chance of a promotion.

Kipp broke Claudes 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, Kipps 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 Kipps trust on her). Meanwhile, Lydia tries to prove that Will hasnt forgotten about their night together and ends up realizing she is the one who forgot about it.

Will leaves his apartment to be taken care by Claude while hes 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 moms 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 its up to Claude to fix things.

Its Valentines Day and Lydia is feeling jealous of Claude over a dozen roses she got from Charlie, whos on a road trip with his father. The next morning, two dozen roses mysteriously appear on Lydias desk, and she wonders who is her secret admirer. Claude finds out its 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.

In celebration of two years in NY, Claude decides to throw a party at her place. But when Will says hell go (a direct result from his publicists attempt to popularize his image), she changes her party from casual to fancy. The only thing she wasnt 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.

Learning that Owen has ""sired"" a child, Claude tries to arrange a get-together between Owen and the dad hes 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 hawks tickets to Wills benefit dinner for a squirrel clinic, Owen gets in trouble with a bookie, and Kipp & Lydia scheme to get free merchandise.