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.

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'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.

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 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.