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.