Mrs. Louder, (Nan Martin) the elderly widow of the Winfred-Louder store's founder, asks Drew (Drew Carey) to lunch. She offers him a job as her personal assistant, with increased pay and a promise that he will be in line to become head of personnel. He isn't sure that he wants to change jobs, but fears that he will be fired unless he complies.
Drew enjoys making connections within the corporate world, and is now allowed to date Lisa because he is no longer part of management. Drew and Lisa (Katy Selverstone) have a tryst in the restroom during the office Christmas party. Drew is demoted to his old job after Mrs. Louder catches them in the act. Meanwhile, Jules Lambermont (Blake Clark) drives Drew crazy with his elaborate holiday lights display.