When Lewis' sister, Janet drops by for a visit, Drew who had a brief fling with her in high school shows a renewed interest and proceeds to date her despite Lewis' reservations. But when things don't go well, he needs to breakup with Janet without incurring Lewis' wrath.
Lewis's sister, Janet (Lisa Amsterdam), moves back to Cleveland with her ten-year-old daughter, Monica (Francesca Marie Smith). 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.