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.
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-Lauder. 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.
Drew discovers Winfred-Louder has a softball team and they won't let him on so he starts his own company team open to all. Steve is on the opposite team and taunts Drew so they agree to play against a game where a beer a base is required.
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 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.
Drew, in exchange to get his job back and so Wick can stay in the US, and Wick get a sham civil union in Vermont. Afterwards, Drew becomes involved in a Trail Scouts troop which he loves, but his sham marriage threatens his involvement.
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.