The Homeless Rock Star

S1 E10: When interoffice fighting reaches a peak, Steve steps up and declares that everyone must switch roles for a day. As everyone adjusts to their new responsibilities, Burke smuggles a homeless woman named Lucinda (Alanis Morissette) into the office so she can paint his office in exchange for a meal. While Burke isn't paying attention, the staffers unwittingly mistake Lucinda for a client and give her a makeover so she's oddly attractive. When Burke realizes Lucinda has been made over, he schemes to set her up with a hard-to-match client, Randall (Michael Hitchcock); however, his master plan backfires when Randall is so taken with her homeless no-care lifestyle that he rids himself of his earnings and stiffs Lovespring on their commission.