Drew worries his physique is holding him back at work when Mr. Wick picks a robust employee to attend a convention in Hawaii instead of him. A guy at the Warsaw overhears Drew's plight and claims to have the solution: a weight-loss pill that activates when taken with beer. He offers Drew a free bottle if he poses for before and after pictures. Days later, Drew is horrified to see his shirtless "before" photo on a billboard in town.

Drew decides to turn over a new leaf by becoming more assertive. He taps into the boardroom to see the footage of his meeting and hear his evaluation. Drew ends up getting more than he bargained for when he and Mimi see Larry and Mrs. Louder having sex in the boardroom. Meanwhile, Mimi still has a confused Mr. Wick living at her house and Kate and Oswald begin secretly dating.

Just when Mr. Wick is getting back on his feet, Mimi tricks him into thinking another storm has hit the city. She continues to run the store by signing Mr. Wick's name on all the orders. Drew becomes suspicious of Wick's disappearance so Mimi issues a memo that says he's fired. With a heavy heart over losing his job, Drew keeps pursuing real estate agent Nicki Fifer (who thinks he's a loser for being unemployed) while Kate and Oswald break the news about their relationship.

The government seizes Drew's house after Larry's antics in the previous episode. They plan to sell it at auction. Drew gets an idea from Nicki to declare bankruptcy on the house to get out of debt and then have Lewis bid on it on Drew's behalf. Tensions erupt as Drew has a difficult time accepting Kate and Oswald as a couple.

Drew is amazed to find out Nicki was overweight in the past but managed to lose 85 pounds. In support of her strict diet, Drew vows to lose 10 pounds. Mimi mocks Drew and claims Nicki lied about her past to pressure Drew into losing weight because she's embarrassed of his appearance. Doubt begins creeping into Drew's mind so he starts searching for proof of Nicki's past weight troubles.

Drew wins the Batmobile in a contest at a fast food restaurant. Nicki and the gang are amazed Drew was offered $200,000 in lieu of the car but turned it down. Drew's outlandish prize starts to cause problems in his relationship with Nicki when she refuses to let him drive the Batmobile when they meet her parents for a dinner date.

Mr. Wick is roped into dog-sitting Mrs. Louder's prized show dog; it's very valuable because of its unique coat and breeding capabilities. Wick ditches the responsibility by leaving the dog with Drew without consulting him. Kate drops the dog off at Drew's and doesn't have time to leave a note. When Drew gets home, he assumes the dog is a stray and takes it to the vet. Kate returns later and is horrified to find the dog shaved and neutered.

Drew's older brother Steve pays a surprise visit; he's down on his luck after going through a broken engagement and losing his job. Kate convinces Drew to give Steve a job in the cosmetics department. One afternoon at work, Drew is astounded to find his brother dressed in women's clothes, complete with a wig; Steve reveals he is a cross-dresser. Upon this discovery, Mr. Wick demands Drew fire Steve immediately.

The gang decides to get the old band back together for a battle of the bands contest at the Warsaw. Kate desperately wants to be lead vocalist but the guys are hesitant because she's an awful singer. The guys run into Herb, an old high school rival, who is confident his band will crush Drew's in the contest. The gang is determined to win but the guys know they won't if they let Kate sing.

Drew's pastor convinces him to volunteer at a seniors' center, where the residents have a reputation for being difficult. Mr. Wick hears about it and convinces Mrs. Louder to require all the employees to "volunteer" at retirement homes for the good publicity. Gus, a resident at the retirement home, talks Drew into taking the seniors to the store so they help with inventory. Gus takes a bunch of photographs and tells a local news station that Drew is abusing the residents. The elderly start picketing Winfred-Louder and Drew is at risk for losing his job.

Winfred-Louder holds a desk-decorating contest for the employees, with the winner receiving two tickets to the Bahamas. Drew creates an entirely edible cubicle and Kate dances on top of her desk. Mr. Wick calls them co-winners and gives them each a ticket. Drew is worried about being alone with Kate because of his feelings for her in the past. Lewis accidentally spills the beans about Drew's fears, which leads an enraged Oswald to stow away on a courier flight to the Bahamas in order to confront Drew.

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 scrape 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.