The store's Dutch owner draws Drew into his plans to demolish Winfred-Louder to build a parking garage.

The gang prepares for its high school reunion. Kate plans to spend all of her time with Patrick, a geeky classmate who is now a wealthy computer software magnate. Lewis poses as Bo Derek's driver at the airport and somehow manages to convince her to be his date at the reunion (as long as he doesn't touch her). Oswald hooks up with his old barber shop quartet. The speaker humiliates Drew by pointing out that he is single, still has the same job, and lives in his parents' house. Drew is confused when Kelly, the former head cheerleader, suddenly expresses an interest in him. Bo Derek explains that he is attractive to women because he is a nice, stable guy. Patrick shows up late, so Drew invites everyone back to the house for beer so that Kate can spend more time with him. An attractive woman gets revenge on Oswald for calling her names in high school (when she was fat) and ignoring her after they made out in his basement. Drew discovers that Kelly leads an extremely dysfunctional

Kate feels extremely threatened when Drew receives a call from Wendy, his recently divorced college girlfriend. Drew assures her that she has no reason to worry, and agrees to have lunch with Wendy. She tells him that she returned to town in the hopes of escaping an obsessive ex-boyfriend. She hasn't worked for years, but hopes that Drew can give her a job at the store to help her get back on her feet. He hires Wendy as his assistant, and tries unsuccessfully to hide the truth from Kate. Kate gets jealous and storms off. While at the Warsaw, Drew receives a call from a panicked Wendy, who fears that her ex-boyfriend has tracked her down. Mimi overhears and suspects that the whole thing is a ploy to get Drew into bed. Drew begins to agree with her after he arrives at Wendy's apartment to find her in her underwear. She claims that her radiator is broken. Even after Wendy's ex-boyfriend shows up, Drew still believes it is a scam. He changes his mind after the guy punches him.

Mr. Wick refuses to let Drew collect unemployment, and keeps saying that he quit even though he was actually fired. An employee objects to Wick's treatment of Drew and gets fired. Drew promises to help him land a new job, and the man offers to give him ten percent of his first month's salary. Drew decides to run an employment agency out of his house, and it proves very successful. Oswald and Lewis express dissatisfaction with their jobs and ask Drew to help them. He believes that he can get both of them work at a new restaurant, only to discover that there is only one opening. Oswald and Lewis are furious, as they have already quit their jobs. They keep pushing Drew to choose between them. Kate suggests that they just go to the restaurant for a tryout. They both fail miserably. Fortunately, Oswald realizes that he never really quit at Global (he went into the wrong office and mooned a blind lady instead of his boss). Lewis returns to DrugCo to beg for his job back.

Oswald's estranged father gets out of prison after a ten-year sentence, but Oswald doesn't want to see him. Drew looks for a part-time job to pay off his credit card debts. Oswald tells him that his father was hired by a real estate company, and asks his dad to help Drew get a job. Mr. Harvey also buys Oswald a bike, and they seem to be making a connection. Drew fails to make a sale for several days. The boss threatens to fire him unless he sells something by the end of the day. Lewis agrees to buy one of the cheaper properties, which a divorcing couple is supposedly trying to unload. He pays cash, so there can be no trace if there is a problem. Drew learns that his boss is a scam artist; he has sold the same property dozens of times, and it is unlivable because of high levels of radioactivity. Drew tells Lewis, but they do not call the police because they do not want to send Oswald's dad back to prison. Lewis and Kate fail in an attempt to get his money back. Drew confirms