Drew is thrilled when he wins the opportunity to give a speech at a retailers' convention in Chicago. He engages in a practical joke war with Lewis and Oswald. The guys play a joke on Sharon, and she promises to get back at them. Drew gets stopped by airport security, which finds a vibrating marital aid in his bag. He is humiliated in front of all the representatives from other stores, and everyone makes jokes and laughs at him during his speech at the convention. Drew assumes that Mimi is responsible. He goes before the board to request her firing. However, Sharon actually staged the joke, with help from Kate and Lewis. She says that she just wanted to feel like one of the gang. Drew is upset with her for jeopardizing his professional reputation. They break up, but Sharon later shows up at his house for their scheduled date, where they apologize. Meanwhile, Oswald gets a promotion to Global Parcel's "angel of death," where he must inform customers about their lost or damaged packages.