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.

Drew worries about passing the physical at work; Doreen still wishes to be like Mimi.

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 becomes an Internet Star after he begins promoting products for Winfred-Louder via 24/7 webcams from his home.

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.

Steve and Mimi get married.

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.

Drew is responsible for Steve and Mimi's truck being stolen so Steve and Mimi set up housekeeping in a trailer in Drew's backyard.

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.

Drew jeopardizes his relationship with Kate by hiring his ex-girlfriend Wendy as his assistant.

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.

Drew and friends are dosed with an anti-alcoholic substance, Lewis and Oswald date sober, and Kate gets a new job.

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.

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.