Season 1: Episode 8: Lewis' Sister
Lewis's sister, Janet, moves back to Cleveland with her ten-year-old daughter, Monica. Drew once had a crush on Janet and was briefly involved with her at summer camp. To commemorate his one-hundredth hiring, the store gives Drew three tickets to a Rolling Stones benefit concert at the Rock and Roll Hall of Fame. Kate is not interested and Oswald has other plans. Kate suggests that Drew ask Janet to go with him. Lewis is adamantly opposed to this idea because he fears that someone will get hurt. Drew ignores Lewis's warning and takes Janet and Monica to the concert. He really likes Monica, who soon joins the store-sponsored basketball team that Drew and Kate are coaching. However, he finds Janet somewhat boring and clingy. Janet and Monica embarrass Drew by showing up at his desk with a picnic and singing about how great he is. Lewis warns Drew not to hurt his sister. When Janet shows up after basketball practice and suddenly proposes, Drew tells her that they should stop seeing each other. She takes the news well, explaining that she knew they didn't have great chemistry, but was desperate for a new relationship. Drew and Lisa, still unable to date, have to settle for brief exchanges at the office. They figure out a way to spend time together by forming a carpool and getting "lost" on the way home.