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.

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.

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.

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.