Drew and Lisa's relationship gets rocky when all they do is argue everyday. On the work front, the Winfred-Louder staff sucks up to Drew because it's employee evaluation day. However, emotions run high when Lisa sees her less-than-complimentary evaluation early and is livid with Drew.
Drew is outraged when the company refuses to promote him to permanent manager and instead hires an Englishman named Nigel Wick. Wick turns out to be a very crooked character when he bribes Drew with the promise of the assistant manager job if he'll be Wick's "bad guy" when it comes to company cutbacks.
Lisa moves in with Drew and it really puts a strain on their relationship. Drew goes to great lengths to avoid going home at night while Kate, who thought Jay was going to propose, is confused and hurt when Jay says he is moving to Minnesota without her.
Drew runs into old high school bully Simon Tate (guest star Norm MacDonald) at the Warsaw. Simon apologizes for how he behaved as a teenager and seems to have changed his ways. Drew gives an out-of-work Simon a job at Winfred-Louder but he soon starts pushing everyone around just like in the old days.
Kate starts dating a new guy named Jack. He interviews for a position in the store and Drew is disturbed to find that Jack thinks he is the devil. Kate is sure Jack is just joking but soon finds out otherwise. When Kate tries to dump him, Jack claims she sold him her soul and says she can never leave him.
Drew is depressed after learning his high school band teacher, Ms. Blankenship, has died. He organizes the band to play a tribute performance for her and is furious when no one takes it seriously. When the gang questions Drew about it, he reveals that he lost his virginity to Ms. Blankenship. He considers the experience very special. However, Drew is dismayed to find out he was not the only male student seduced by the attractive music teacher.
Drew meets Bonnie (guest star Caroline Rhea) at the Warsaw and brings her home to see his brewery. Once she finds out he doesn't have a permit, she admits that she's a zoning inspector and has to report him. Drew organizes a party and sells maps to the location in order to give away the beer. Bonnie shows up at the party and threatens to arrest Drew and the gang for soliciting to sell alcohol. The party disbands but things get complicated when Drew and Bonnie sleep together after everyone leaves.
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.
Drew feels left out when popular salesman Dexter Roberts hang outs with all the other employees and embarrasses Drew in front of the whole store. Drew finds out Dexter is throwing a huge company party and only Drew and Mimi aren't invited. The two put aside their differences and decide to crash the party and ruin everyone's fun.
Drew inadvertently agrees to organize a wedding shower for his ex-girlfriend Lisa when he mistakenly believes the bride is an elderly employee also named Lisa. Lisa's fiancé Trent, according to Drew's new system that ranks employees by performance, is first in line to be fired from the store. Lisa thinks Drew is acting out of spite because he hasn't moved on but Drew insists it's because Trent is a poor employee. Drew talks with Trent and is unnerved when Trent has an epiphany and decides he wants to call off the wedding.
Drew is worried when he hears about a hurricane hitting Florida near where his parents live. Unexpectedly, his parents show up at his place and admit they've been traveling in their Winnebago because they lost their house. Worst of all, Beulah lost her life savings in a land development scam. Drew plans to let them stay over for a few weeks until the lawsuit is settled but is torn about what to do when his parents lose the case.
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.
Oswald and Lewis plan their usual prank war for Drew's birthday and tease Kate for not being able to compete with their elaborate jokes. Meanwhile, Drew volunteers to update the store's training films in hopes of earning a promotion. Kate hopes to win the prank war by tampering with Drew's training video and showing it at his birthday party. Unfortunately, Drew unknowingly takes the tampered tape to work and presents it to the board.
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 girlfriend from junior high school. 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 also 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 2,700. 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 do a drag-off in the streets with Mimi and her Priscilla cronies.