Lord Mercer announces that he is making his 19-year-old daughter, Milan, the new store president. She is disgusted, but he hopes that the job will teach her some responsibility. Lord Mercer tells Drew that he must make sure Milan does a good job or lose his co-manager position. She messes up a negotiation with a union by bringing in her boyfriend, D'Artagnan, and groping him the whole time. Drew asks Kate to talk to Milan and convince her to focus on her job instead of devoting all her time to her boyfriend. Milan takes her advice and gets dumped. She forces Drew to go work at the docks. Kate feels bad for Drew and agrees to try to get D'Artagnan to take Milan back. Kate instead sleeps with D'Artagnan just because he gives her some stupid look. Milan plans to give Drew his old job back, until she learns what Kate has done. Milan vanishes on the day that her father has come in to check on her progress. Drew sees her on the edge of the building preparing to jump.

Lord Mercer refuses to show concern for Milan, claiming that she regularly threatens to kill herself to get attention. Drew gets her to come off the ledge. Drew is upset when his father refuses to congratulate him for his promotion, instead sending him a fish wrapped in the newsletter that announced his new position. Lord Mercer fires Milan for repeatedly refusing to show up for meetings. She feels that she has no reason to make an effort because her father is never satisfied by anything she does. Drew, inspired by his own situation, pleads with Lord Mercer to give Milan another chance. He promises to help her do a better job running the store. However, Milan only knows how to do one thing--party. She throws a rave in the store. It seems to be a disaster, but actually boosts sales considerably. Lord Mercer still disapproves because raves are bad for the store's reputation. Milan decides that she doesn't always need to seek her father's approval. Meanwhile, Lewis inadvertent

Drew spends his entire vacation home sick with the flu. Milan prepares for her 19th birthday party, which will take place in Spain and feature many supermodels. Lewis and Oswald decide to apply for second jobs as airport security guards so that Oswald can afford his nursing school tuition. After Drew whines about never getting to travel anywhere, Milan invites him to her party. Oswald and Lewis get the jobs, and are extremely overzealous and incompetent (big surprise). Drew tries to cut in line and race through without undergoing a security check. He gets hauled off to a holding cell and misses his flight. The supervisor refuses to let him board another flight because he has been arrested so many times. Drew has Kate distract the supervisor by pretending to have lost a baby. He tricks Oswald and Lewis and runs past them to board the last flight to Spain. The plan has mechanical problems and lands in Greenland. He thinks his luck has changed when he meets a beautiful woman, b

Milan fixes up Drew with her mother, Lindsay, because she wants her to finally meet someone who isn't just after her money. Drew makes the mistake of allowing Lindsay to drive his car, and they are trapped for several hours after she crashes into a ditch. Lindsay finds Drew's lifestyle charming, and wants to continue seeing him. She is scheduled to leave town a few days later, but suddenly announces that she is moving to Cleveland. Drew is alarmed to learn that Lindsay would lose her $500,000 per month alimony if she ever re-married. He predicts that she will soon grow tired of the novelty of living like a poor person. He challenges her to spend one week in his world. She tries her best to adjust to a simple lifestyle, but really doesn't take to it. She begins breaking out in rashes and losing her hair. Drew decides that he is in love with Lindsay for some reason. After he tells her this, she announces that she is leaving. She never really liked him that much, and cannot sur

Lord Mercer and Milan celebrate their financial success by giving the employees fancy new desks. They later learn that their accountant has cleaned them out, and have to lay off a bunch of employees. Drew, Mimi and Mr. Wick are forced into duty on the sales floor, where Drew sells underwear. When the store continues to flounder, Lord Mercer converts it into a discount outlet. Nicki sends Drew a gift and claims to have forgiven him. Drew is suspicious, but decides to meet with her. She has gained back all of her weight and is homeless. She tries to shoot Drew, but drops her gun. Drew feels responsible for her problems and offers to let her stay with him. Nicki finds a knife in the kitchen and thinks about stabbing him, but is distracted by cheese and decides that she can kill Drew later.

As Drew prepares to marry Lily, his mother notes how upset Kellie seems and realizes that she has strong feelings for Drew. She believes that Drew feels the same way about Kellie. Drew and Lily go through with the wedding, but the union proves to be a brief one when they realize that they really are not right for each other. Drew winds up sharing a dance with Kellie.