Drew's girlfriend Sharon hints at moving in with Drew but senses he actually loves Kate because in his diary he refers to her as Kate. Drew swears he loves her and has her build him a Y2K shelter but has to try another grand gesture.
Drew wonders if Sharon is cheating on him and Mimi and Lewis and Oswald reinforce the idea. Lewis comes up with a harebrained plan to get in to the first Browns game, who've been gone from Cleveland for 3 years, that leads to a discovery.
Drew, Kate, Lewis and Oswald bump bumpers with a policeman who discovers they have firearms and much cash (for Y2K) in their trunk. A judge applies a law that deems them as gang members and orders them to not associate with each other.
Lewis scams Bo Derek into coming with him. Kate reconnects with a former nerd now wealthy and good-looking. Oswald meets a beautiful classmate he doesn't remember but she remembers him. Drew cozies with a cheerleader with a really bad side.
Mimi's pranks so enrage Drew he makes threats. Later in the parking garage Drew is attacked by a bee while driving and nearly runs over Mimi. Police plan to formally charge Drew but his brother Steve urges Mimi to drop any charges.
A pothole in front of his house prompts Drew to launch a ballot initiative to fund street repairs. When the polling place burns before the election, Drew volunteers his house as a replacement.
Kate looks for right moment to declare her love while Drew looks to declare his love for her, each unaware of the other's intentions. At Steve and Mimi's engagement party they both keep getting stymied just as they have their chance.
Drew starts having intermittent severe stomach pain. Kate notices they started at the same time Steve and Mimi discussed actual wedding plans. The pains get so bad that Drew is rushed to the hospital where Kate discovers the real cause.
Kate and Drew finally go on the first date, but after Kate falls asleep next to Drew afterwards he assumes she was bored by him so he decides to make their next date more interesting.
At a Winfred-Lauder fashion show, Drew has arranged for a board member to speak. His insensitive speech creates a uproar, and everyone blames Drew. To counter the problem, he uses a company resource book for a play to promote sensitivity.
There is a new management team at Winfred-Lauder and Drew is told he can hire an assistant. He reluctantly hires Kate but her abrupt manner causes problems and Drew is forced to fire her.
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 Emmys, 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.
