After butting heads with a grouchy office worker, Claude fears that she'll eventually become like her. Meanwhile, Kip gives Owen an Armani suit as collateral for a loan; and Lydia obsesses over whether she'll be included in Will's autobiography.
While awaiting a second date with Charlie, Claude reluctantly agrees to go out with Will's godson, Oliver. Meanwhile, Kipp schemes to get a promotion by sucking up to the prepubescent son of the president of the network.
Claude produces an embarrassing anchorman demo reel for Kip. Meanwhile, it's the anniversary of Lydia's fling with Will and she tries to determine if he remembers it. Owen gets hooked on the Dr. Phil show and uses his newfound assertiveness to score executive potatoes.
Claude tries to keep her relationship with Charlie a secret -- but her friends are determined to find out what she's hiding. Meanwhile, neither Kipp nor Lydia get what they bargained for when they go looking for mentors.
When Claude's asked to watch Will's apartment for the weekend, all of her coworkers invite themselves over. Meanwhile, Kipp and Claude's rivalry is put on the back-burner when he discovers something shocking on Will's telephone.
Will's new girlfriend rubs Claude the wrong way, so she meddles in their relationship. Meanwhile, Kipp and Lydia find themselves sucking up to Owen and Ramona, in hopes of scoring VIP access to an exclusive party.