The Buzz Beer tank explodes, causing beer to rain down all over the Clemens' yard. Drew invites them over for dinner to convince them not to sue. Janet talks Greg into investing in Buzz Beer so the gang can replace the tank. Greg agrees on the condition he can call all the shots. The gang is forced to work constantly so Drew decides to get Greg drunk to loosen him up.
Mr. Wick is panicked upon finding a memo he thinks is about firing him. Wick convinces Mimi to plot a phony sexual harassment scheme with him. Mimi will claim Wick harassed her, file suit against the store, and the both of them will split the winnings on a tropical island. Wick makes a "pass" at Mimi in front of Drew. When Drew refuses to be bribed into silence, Mrs. Louder demotes him to the sales floor. Drew becomes suspicious of Mimi and Wick when he finds out they opened a joint bank account in the Cayman Islands.
Mrs. Louder asks Drew to make a toast at birthday party honoring her late husband. The best toast wins 500 shares of company stock. Drew struggles with what to say because Mr. Louder was a terrible person. Oswald and Lewis agree to attend the party to support Drew but Nicki doesn't want to go because she's gained weight. Nicki finally shows up and Drew decides to make her feel special by dedicating his speech to her. Drew's plan proves disastrous as the spotlight is aimed right at Nicki while she's pigging out.
Kate hopes to get promoted to wardrobe buyer but Mrs. Louder doesn't think she has enough class for the job. She and Drew organize a salon at his house where everyone can discuss social and political issues. Mrs. Louder pays a visit to the salon and ends up in a heated argument with Kate over Internet censorship.
Oswald announces his plans to move in with Kate. Drew's jealousy gets the best of him and he ends up in an argument with Kate. Oswald accuses Drew of pining for Kate and then insists he and Kate are more compatible than Drew and Nicki. The guys decide to test their relationships by slipping in questions from a magazine compatibility test during their Valentine's Day double date.
Drew and Oswald buy their engagement rings. Drew plans to give the ring to Nicki at dinner when he meets her parents for the first time. Drew is stuck eating dinner alone with the Fifers when Nicki gets snowed in at her sister's. One tense evening ensues as the Fifers blame Drew for their daughter's shortcomings and eventually start arguing amongst themselves about their lackluster marriage. Mrs. Fifer decides to move out while Mr. Fifer tries to convince Drew to help him meet new women.
The gang is bummed when Drew's refrigerator breaks down. Drew convinces Mr. Wick to put up a beautiful new fridge as a prize in the annual employee games. Drew and Nicki team up in hopes of winning a new fridge but heavy competition from the undefeated Mimi and Larry turns the games into a serious fight to the finish.
Drew and Nicki plan to videotape themselves having sex. The next morning, Drew's parents come to town to celebrate his engagement. Drew tries to tell his mother about a problem with his relationship but is constantly interrupted. Drew eventually tells Beulah he has called off the wedding. She begs Drew to go through with the bachelor party and break the news to George afterward because of how depressed he's been.
Lewis confiscates a sex drug from DrugCo after nearly being attacked by several monkeys who had used it. The drug is accidentally spilled into a batch of green Buzz Beer being prepared for St. Patrick's Day. Everyone at the Warsaw inadvertently drinks the tainted beer with startling results. Drew prepares to be the sole witness in Mimi's "sexual harassment" case while under the influence of the sex drug.
After Mr. Wick is injured at work during an elaborate and cruel plan to fire an employee, Drew is placed in charge for the week. Drew adopts a "no firing" policy that works wonders until employees start taking advantage of Drew's generosity. The store starts to fall to ruins just as Mrs. Louder's return looms.
A gorgeous handywoman named Sharon visits Drew's house to fix several appliances that were broken during a drunken celebration the night before. Oswald and Lewis push Drew to ask her out while Kate is sure Drew is on the rebound and likely to hurt Sharon. Drew finally gets the courage to ask Sharon out but she insists on being only friends.
Drew meets a woman at the Warsaw who recommends he attend her dating advice service. He agrees only to be publicly embarrassed when the instructor shows a videotape of Drew's date as "a teaching aid". Drew is the laughingstock of the class despite the fact that most of them are career losers who are still virgins. Drew seeks the help of the Better Business Bureau to shut down the advice center but ends up needing class advice when he scores a date with a Bureau employee.
It's Drew's turn to host the family barbecue for all the Carey cousins. Drew's 18-year-old cousin Kristen comes to the party while looking at colleges. Kristen asks Drew if she can stay at his place until a dorm room opens up at Cleveland State in the fall. Drew agrees but is horrified when Kristen starts dating Mr. Wick.
Mrs. Louder calls Drew to tell him he's been chosen to coordinate hiring for the new stores in Europe. The catch is Drew has to get to the boardroom within 10 minutes to secure the position. The universe seems to be against Drew's success as numerous obstacles, including a broken elevator, an irate customer, and a blocked staircase, get in his way to the boardroom.
Kate and Oswald start planning their wedding but find they won't be able to afford many luxuries. The gang heads to a discount bridal shop and discovers Kate's dream wedding dress costs $5,000. Kate is devastated but Drew is determined to see her happy. He manages to scrap up enough money to buy Kate the dress. The problem is: Oswald plans to surprise Kate with a knockoff dress he bought for her.
Lewis forces Oswald and Drew to shake and make up. Kate tries to come up with a way to tell Oswald she isn't in love with him anymore and wants to call off the wedding. Drew urges Kate to tell Oswald to his face and get it over with. Kate's plan is thwarted when Oswald throws a surprise wedding ceremony for her in Drew's backyard. Kate is at odds with whether to avoid humiliating Oswald or to be true to her heart.
After a string of mishaps at work, Drew begins to suspect someone is out to get him. Everyone thinks he's paranoid until security tape footage shows a group of three men discussing how much they hate Drew and how they've been plotting pranks to make him miserable the past ten years. Drew decides to take a stand and find out why the mystery men loathe him so much.
Drew is in charge of entertaining a group of investors from Vietnam. While Drew's band plays for the investors at a local hotel, the manager asks them to replace the regular hotel band. Drew is torn whether to focus on his career at the store or become a musician full-time with his band.
Drew decides to go blonde and must endure the snide remarks from friends and co-workers. When Larry discovers that someone has been doing cocaine in the men's room, Mr. Wick forces Drew and Mimi to take urine samples from all the employees for drug testing.
Mrs. Louder offers to let Drew fill in as store manager while Wick in is rehab but Drew turns her down in favor of spending more time with his band. Drew's band, the Horndogs, is offered the chance to go on a tour of every Ramada in the state. Drew wants to quit his job at the store for good but Kate and the other employees plead with him to stay.
Drew's groupie girlfriend Darcy dumps him when she discovers that Drew isn't a full-time musician. He drowns his sorrows by starting a steamy online affair with a mystery woman. However, Drew starts getting suspicious when his internet sweetheart admits to working at a department store and collecting troll dolls. Could his online love really be Mimi?!
Steve shows up at the Warsaw dressed in drag and Drew stands up for his brother when a bar patron behaves obnoxiously. Steve's transvestite friends start coming to the Warsaw as a show of support for Steve. Drew and the gang become annoyed when the Warsaw is so inundated with cross-dressers that all other customers stop coming to the bar. Steve is livid when the bartender starts a policy of discounted drinks "for real women only" and is even more appalled when Drew refuses to back him up.
Drew claims to be happy for Nicki when he finds out she's getting married. When he gets an invitation to her wedding, the gang is sure it's just a "courtesy invite" and discourage him from going. Drew decides to take his new date to the wedding and ends up making a fool of himself when Nicki's parents make known how little they think of Drew.
Drew is in charge of selecting the Winfred-Louder employee of the year, who will win a trip to Hawaii. For the first time ever, a non-Louder may actually win because all the Louders have seemingly already won. Oswald receives his check for testing the breast implants and decides to repay his friends for all the money he's borrowed over the years. When Drew's car is totaled, the gang pools all their money to buy him a sleek new VW Bug.
Drew pulls off an elaborate practical joke on Mimi and brags she will never be able to retaliate. Days later, Drew wakes up on the Great Wall of China with no money or passport. He is left clueless and wandering around China in search of the U.S. embassy. Meanwhile, Kate, Lewis, and Oswald become concerned when they find out Drew never made it to his business trip in Winnepeg and suspect Mimi has something to do with his disappearance.
Kate takes a paid house-sitting gig after losing her latest job. She meets handsome plumber Scott while at the house and the two are instantly attracted. When the house owner is forced to leave her two children with Kate, Scott offers to help out. The group starts acting like a real family and Kate gets a little too carried away with the fantasy.
Drew signs up for night school classes to pursue a master's degree. In class one evening, Drew meets Celia, an attractive 62-year old, and they get on well as study partners. When mutual feelings emerge between them, Celia begins to distance herself for fear Drew will become embarrassed of her.
Drew's parents arrive for a surprise Christmas visit. They assume Celia is the maid and Drew is hesitant to tell them the truth. To make matters worse, Celia's hostile son Chip shows up in the middle of the night to join the holiday festivities.