Drew may have to terminate his affair with Lisa or risk job termination when the store bans interoffice dating. His solution? Ask Kate's boyfriend to pretend he's dating Lisa, to throw co-workers off the track.

Drew again finds his work coming between him and Lisa, when his negative evaluation of her job performance causes her to reevaluate their relationship.

Drew serves as acting store manager while also fulfilling his regular duties. He is outraged when the store declines to make him the permanent manager, instead hiring Nigel Wick, an Englishman who makes it clear that he would rather be anywhere but Cleveland. Wick makes a stamp of Drew's signature and makes it appear as though Drew is responsible for cost-cutting measures such as the elimination of employee discounts. He coaxes Drew into agreeing to be the ""bad guy"" by offering him a promotion to assistant manager and a new desk. However, Drew draws the line after Wick tries to fire all of the employees with seniority right before their pensions kick in. He claims that the employees are staging a revolt, and Wick wins the staff's approval by eliminating all of ""Drew's"" cutbacks. Oswald and Lewis search for a way to fill a large order of Buzz Beer, which is due in just a few days. They put the neighborhood children to work bottling and delivering beer, much to Drew's horror.

Lisa moves in with Drew, bringing an assortment of pets that includes a toilet-trained cat. They begin to really get on each other's nerves, and Drew goes to great lengths to avoid going home at night. Jay tells Drew that he is considering an offer to run a Dairy Queen in Minnesota with his brother. Kate comes to believe that Jay is going to propose, and realizes that she must reject him. She is bewildered when Jay simply tells her that he is moving and does not even ask her to come with him. Drew tries to console the furious Kate. He drives around with her all night and eats french fries. He finally goes home to find a note from Lisa saying that she has realized that Drew is uncomfortable and has gone to stay with a friend. He dances around to celebrate the fact that he is alone, unaware that Lisa hasn't left yet. She confesses that she is also unhappy, and they have an amicable break-up. She lets him keep her handicapped dog, Speedy. Drew drives Kate around as she breaks th

Wick orders Mimi to begin wearing less make-up and more conservative clothing, as he doesn't want her representing him with her current appearance. When she refuses, Wick banishes her to the archives in the sub-basement. She tries to get revenge by wreaking havoc throughout the store. When Drew accidentally spills beer on a large man at the Warsaw, another man saves him from a fight. He turns out to be Simon, a bully who tormented the gang throughout high school. He apologizes for his actions and seems to have changed his ways. Simon is out of work, so Drew hires him as Wick's new assistant. Simon soon begins pushing everyone around, and even Wick becomes terrified of him. Wick decides to bring back Mimi, regardless of her appearance. He is too afraid to fire Simon, and leaves the task to Drew. Lewis, Oswald and Kate encourage Drew to stand up to Simon, claiming that bullies are really cowards at heart. Although Simon beats him up, Drew manages to fire him. Mimi doesn't wan

Kate begins dating Jack, a guy that she met at the Warsaw. He interviews for a job at the store, and Drew is disturbed to learn that he thinks he is the devil. He has even taken out credit cards under the name ""The Devil."" Kate is certain that this is a joke, but soon discovers otherwise. When she tries to dump Jack, he claims that she has sold him her soul. Drew puts his own soul on the line and challenges Jack to a game of pool, but it doesn't go very well. Kate confronts Jack and says that he claims to be the devil because he is afraid that women will dump him if he acts like himself. He mocks her, so Drew prepares to beat him up. However, Jack loses interest when he learns that Kate lied about being a virgin. He leaves in disgust. Wick orders all of the staff to wear costumes for Halloween. Drew dresses as Mimi, who is outraged when he wears an outfit that she had already purchased.

Drew, Lewis and Oswald learn that their high school band teacher, Ms. Blankenship, has died. Drew seems to take the news especially hard. He organizes the band to put together one last performance for her, and becomes furious whenever anyone insults Ms. Blankenship. His friends ask for an explanation, and Drew reveals that he lost his virginity to her. He considers the experience to be special. However, he soon learns that the teacher regularly seduced her male pupils. Drew receives another shock when Kate and Oswald confess that they slept together once in high school. Drew feels like a fool because he was unaware of these secrets. Kate tries to cheer him up by proposing a secret of their own. She declares that they should get married if they are both still single by a certain age (which Drew keeps trying to lower).

Drew catches the eye of an attractive stranger at the Warsaw. The woman, Bonnie, agrees to come back to his house to see his brewery. After she learns that he does not have a permit, she reveals that she is a zoning inspector and says that she must report him. Mimi (for a fee) suggests a way that Drew might get out of the situation. She says that the gang could organize a party and sell maps to the location, then give away the appropriate amount of beer. Bonnie comes to Winfred-Louder to apologize to Drew, and agrees to attend his party. She brings a policewoman friend to the gathering. Unfortunately, she threatens to arrest Drew and his friends for soliciting to sell alcohol unless they shut down the party and return everyone's money. Bonnie and Drew sleep together. She feels bad about causing him so many problems. She recommends that he get signatures on a petition and appear before the city council to request a change in the zoning laws for his neighborhood. The council h

Drew is upset when Bonnie refuses to go out on dates with him in public. She always wants to stay over at his place and order take-out. Drew thinks Bonnie is concerned about his financial situation but he wants to do something special for her. Drew surprises Bonnie at her apartment with a gourmet meal, only to find out she's married.

Drew's hopes of a relaxing holiday weekend are crushed when Mr. Wick makes Drew in charge of Winfred-Louder's Thanksgiving Day parade. Crunched for time, Drew has to make a deal with Mimi that she can be the "snow queen" in the parade if her father's trucking company supplies the equipment for the floats. Unfortunately, Mr. Wick chooses someone else to be grand marshal and Mimi sabotages the parade.

An employee is killed by a speeding car while trying to cross a busy intersection in front of the store. Dexter K. Roberts, a popular salesman famous for his great parties, is brought in to take over her job. Drew feels left out when everyone leaves to have lunch with Dexter while Drew is in the copy room. Dexter then embarrasses Drew in front of the staff by using him as the guinea pig for his magic tricks. Dexter throws a big party for his co-workers, and even invites Lewis and Oswald. Drew and Mimi are the only ones who do not have invitations. They run into each other at the Warsaw that night and discuss the pain of being outcasts. They become furious and decide to crash the party and ruin everyone's good time. Dexter reveals that he had actually left invitations for Drew in his pockets during the magic trick. However, Mimi was not invited because of her attitude. She wants to trash his house, but Dexter says that he has called the cops and orders her to leave. He pleads

Kate alerts the guys to the fact that a hurricane has struck the near the neighborhood where Drew's parents live in Florida. As they watch the news report, Drew's parents suddenly show up at his house in their Winnebago. They have been on the road since losing their house for failure to make payments. They finally admit that Beulah lost their life savings in a land development scam. The Careys plan to stay with Drew for a few weeks until they receive their claim in a class-action lawsuit. Unfortunately, they lose the case. George and Beulah take over the house and prevent Drew from having any privacy. After his parents spoil a date, he begins spending all of his time at the store. He finally resolves to ask his parents to leave by laying a guilt trip on them. They prove too tough to crack, and Drew ends up staying with Lewis and Oswald.

Drew is getting fed up with the filthy, unsafe conditions in Oswald and Lewis' apartment and threatens to take their landlord to court. But when the landlord finds out Drew has been living with the guys without a lease, he evicts all of them. The three of them end up on Kate's doorstep and she reluctantly agrees to let them stay with her for a few days. Everyone pressures Drew to stand up to his parents once and for all and take back his house.

After realizing there is no way to profit from Buzz Beer, the gang decides to shut down the brewery and throw a party with free beer to get rid of their supply. Drew meets a woman at the Warsaw and invites her to the party but can't remember her name or number. Mimi puts a flier about Drew's party in the Winfred-Louder newspaper as revenge for an earlier prank. Drew's hopes of finding his mystery woman dwindle when everyone in the city of Cleveland (including the mayor, Browns quarterback Bernie Kosar, Little Richard, and Joe Walsh) shows up at his house for the party.

Drew's plans for a promotion may be put on hold when Kate plays a birthday prank on him and alters training videos he made to impress the store's board of directors.

Drew's down-payment on a car bounces because of a bad check at a garage sale. He finds out the woman who wrote the check was Kyra, his junior-high girlfriend. She claims her roommate wrote checks from her account to cover his gambling debt. Drew invites Kyra to stay with him but begins to doubt her when his car is repossessed after her second check bounces.

Winfred-Louder employees risk their lives get to work each day because the crosswalk from the parking deck to the store is at an intersection near the freeway. When a member of the Optimists Club is severely injured while trying to cross, Drew demands the store build a skywalk to the employee garage. When his complaints are ignored and Lewis and Oswald are hurt while trying to cross, Drew decides to take drastic measures by going on a hunger strike.

Drew returns disheveled and frustrated after a convention in Las Vegas. After losing his luggage and all of his money, a waitress named Diane took pity on him and they went out for drinks. She took Drew to a rock and roll chapel to get married and he went through with it, thinking it was a drunken prank. Unfortunately, the ceremony was legal. Diane admits she needed to get re-married in order to keep custody of her two kids. She convinces Drew to pose as her husband for a week to fool the social worker.

Drew finds out Speedy's hip problem is getting worse but there's hope in a new operation that could restore the dog to his old self. The problem is the operation costs $2700. Nora recommends Drew use his company insurance to pay for it. Winfred-Louder has same-sex health benefits; all Drew would have to do is claim the operation is for his lover. Drew agrees but ends up having to prove he is gay by hiring Oswald to play his lover "Aaron".

Earl is released from prison and swears he's a changed man. Drew is ill at ease when Earl moves in next-door and starts watching his every move. Earl claims he is observing Drew so he can assimilate back into society. Eventually, Earl starts dressing like Drew and even remodels his house to look exactly like Drew's. Everything comes to a head when Earl pulls a gun on Drew and the gang, admitting he wants to kill Drew and take over his life.

The gang discovers someone else is marketing a coffee-flavored beer called Cap-Beer-Cino. The owner, Chris Vanderkamp, openly admits stealing the idea but has enough lawyers to keep him in the clear. Cap-Beer-Cino becomes a sensation at the Warsaw, which leaves the gang desperate for business.

When the employee representative to the board is forced to retire, Drew, Mimi, and Larry are thrilled over the possibility of taking over the position that offers a considerable raise and requires little work. The competition to impress Mr. Wick, Mrs. Louder, and the board of directors turns from friendly rivalry to an outright brawl.

Kate is annoyed the guys offered a date with her as a prize in a contest for Buzz Beer. Mr. Wick finds the winning bottle cap and Kate reluctantly goes through with the date. The guys are stunned when Kate and Wick seemingly fall for each other. Little do they know, Kate and Wick are playing a prank as revenge for the contest. However, Mr. Wick may not be pretending.

After a disastrous trip to New York to sell Buzz Beer, the gang makes a shocking discovery: The Rocky Horror Picture Show (1975) has been replaced as the weekend midnight movie with The Adventures of Priscilla, Queen of the Desert (1994), leading to a drag-off in the streets with Mimi and her Priscilla cronies.

Doreen, a ""little person"" who works at the store, chooses Mimi as her idol and begins emulating her dress and behavior. Mimi is a little freaked out, but soon takes to the idea and has Doreen help her play pranks on Drew. Sharon takes note of the fact that Kate can get Drew to do whatever she wants without having to make much of an effort. The store's computers fail a test for Y2K compliance, and a glitch causes excerpts from Drew's diary to appear on all the computer screens. A panicked Drew seeks the aid of the store's computer expert, Hal. He convinces Drew that there will be a massive computer failure and total chaos on New Year's Eve. Drew and the gang ask Sharon to build them a bomb shelter. Lewis carries his life savings ($37,000) around in a garbage bag. Mimi and Doreen print out copies of Drew's diary and sell them at the Warsaw. Sharon discovers that in the passage where Drew described sleeping with her for the first time, he accidentally wrote Kate's name. She conc