Less than Perfect Season 2 Episode 1 Choices (2) ( Air Date 2003-09-23 ) Genre Comedy category. Overview "At Will's urging, Claude takes a job as Mr. Elliot's assistant, leaving her position to be filled by Kipp -- who Will can't stand. Meanwhile, Lydia unsuccessfully tries to impress Mr. Elliot; Ramona and Owen fight over a lunchroom meal plan; and Carl hangs around the office because he locked himself out of his apartment.".