At a Winfrid-Lauder fashion show, Drew has arranged for Board Member to speak whose insensitive speech creates a uproar and everyone blames Drew. To counter the problem e uses a company resource book for a play to promote sensitivity.
New management at Winfrid-Lauder fires Mimi so she and Steve buy an RV trailer for a move to near Dollywood. Drew is careless and lets the truck get stolen so the trailer stays in his backyard. Life with Mimi breaks Drew but he has a plan.
Kate tells Drew she's ready to take the next step. But when they get together, Drew's insecurity goes over the top because Kate says that an unsuccessful experience could ruin the relationship. They try again but Drew sprains an appendage.
Management wants Drew to hire the new regional manager but refuses his request to be Human resources manager. Wick offers him the position of store manager if he is picked for the position. Drew agrees and finds he's dealing with the devil.
Drew wants to sell Buzz Beer to his new boss who wants to set up his brother-in-law with a business. However, Drew has a difficult time convincing the rest of the gang to sell. Episode intentionally has many errors for viewers to identify.
Mimi puts Antabuse in a big cookie and gives it to Drew, making it seem to be from Winfred-Louder. Unaware, Drew shares it with the gang. In forced sobriety, Lewis and Oswald meet former alcoholic women and Drew pops a big question to Kate.
Oswald hears from a girlfriend who tells him they have a son from their teenage years. But before they meet, Drew sees him and notices he bears a strong resemblance to Lewis. Upon questioning, Lewis comes clean but is he really the dad?
Wick returns as a mail boy and vows to Drew he's scheming to take back store manager from him. Mimi uncovers his scheme but Drew still gets sabotaged. Drew makes an unexpected alliance against this foe and then a golden opportunity arises.
Because their schedules clash, Kate moves in with Drew but sees Speedy as deliberately interfering with her time with Drew. After Kate has Drew put Speedy outside there is an incident and Drew brings an animal psychologist that Lewis knows.
When Drew discovers that Winfred-Louder has a softball team they haven't let him join, he starts his own open-to-all company team. Steve taunts him from the opposite team so they agree to play each other in a beer-a-base game.
Realizing that he's healed "down there," Drew lets Kate know, but she's come to realize that she's been terrible to all her past loves; Oswald has started a group for them. Episode ends with some over-the-top Fellini-style symbolism.
Drew laments the show's lack of Emmy's but vows no tear-jerking story. Kate is rushed to the hospital and lapses into a coma. Lewis agonizes in single-spotlight soliloquies about his insensitivity. Oswald is a kleptomaniac. Mimi is OCD.
Drew's rich Uncle Cecil, a movie buff, dies, leaving $10,000 to Drew on the condition--based on Buster Keaton's "Seven Chances"--that he get married within 72 hours. Drew and Kate are already engaged, so a quick wedding should be simple, except that Oswald and Lewis get involved, and things go haywire.
Drew tells Lewis and Oswald of secret shopper jobs so they quit their current jobs. Then Drew learns there is only 1 position so the 2 compete. Many "Whose Line Is It?" cast appear doing improv dialogue and songs and Jay Leno appears.
To cheer up Drew, Steve introduces him to Jenny. They hit it off but then Steve reveals Jenny is Mimi's cousin. Kate discovers Drew has moved on and gets drunk with Wick. Drew and Jenny go back to Drew's place, as well as Kate and Wick.