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Episode List


Season 5

22 Sep. 1999
Y2K, You're Okay
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.
29 Sep. 1999
Drew Goes to the Browns' Game
Drew wonders if Sharon is cheating on him and Mimi and Lewis and Oswald reinforce the idea. Lewis comes up with a hare-brained plan to get in to the first Browns game, who've been gone from Cleveland for 3 years, that leads to a discovery.
6 Oct. 1999
Drew and the Gang Law
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.
13 Oct. 1999
Drew's Reunion
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.
20 Oct. 1999
Drew's Physical
Drew worries about passing the physical at work; Doreen still wishes to be like Mimi.
27 Oct. 1999
Drew Tries to Kill 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.
3 Nov. 1999
Red, White and Drew
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.
10 Nov. 1999
Drew Live
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.
17 Nov. 1999
Drew Cam
Drew becomes an Internet Star after he begins promoting products for Winfred-Louder via 24/7 webcams from his home.
24 Nov. 1999
Drew's Stomachache
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.
1 Dec. 1999
Steve and Mimi Get Married
Steve and Mimi get married.
15 Dec. 1999
Drew and Kate's First Date
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.
5 Jan. 2000
Drew and the Racial Tension Play
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.
12 Jan. 2000
Kate Works for Drew
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.
2 Feb. 2000
Mimi Moves In
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.
9 Feb. 2000
Do Drew and Kate Have Sex?
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.
16 Feb. 2000
I Dishonestly Love You
Drew jeopardizes his relationship with Kate by hiring his ex-girlfriend Wendy as his assistant.
23 Feb. 2000
Drew Goes to Hell
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.
1 Mar. 2000
What's Wrong with This Episode III
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.
22 Mar. 2000
The Gang Stops Drinking
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.
29 Mar. 2000
Oswald's Son
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?
12 Apr. 2000
Mr. Wick Returns
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.
26 Apr. 2000
Kate vs. Speedy
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.
3 May 2000
Beer Ball
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.
10 May 2000
Drew and Kate Boink
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.
17 May 2000
A Very Special Drew
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.

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