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.

Mimi runs into Nicki at the store's bridal registry. Nicki has to race upstairs to try to keep Mimi from telling Drew about her wedding plans; she had wanted to share the news herself. He claims that he is happy for her. Drew is surprised when Nicki sends him a wedding invitation. Kate, Lewis and Oswald insist that it is only a courtesy invitation and try to discourage him from attending. They plan to stay away as well, but Drew urges them to go to the wedding. Oswald is really excited because the wedding is on a boat. Drew goes on a date with a video store clerk, but suddenly decides to take her to the wedding. Nicki's parents cannot believe that he had the nerve to show up. Drew makes a complete fool of himself while trying to prove how mature he is. He actually manages to give a toast that isn't totally humilating, but throws out his back while trying to show up the groom on the dance floor. As Drew waits for the helicopter to lift him off the boat to take him to the hosp

A flashback show that features clips of some of the series' music-video segments.

Drew is finally released from the mental institution. On the day of his release, he runs into Nicki at the Warsaw. She reveals that she is divorced, and feels she made a mistake in letting Drew go. Kate worries that Nicki is going to hurt Drew again. Kate, Lewis and Oswald try to create a distraction to help Drew get away, but he assures them that he is all right. After his friends leave, Drew suddenly proposes to Nicki. She accepts, and they marry in Pennsylvania. Drew's friends cannot find him for several days. Kate admits to Lewis and Oswald that it made her very jealous to see Drew with Nicki. She realizes that she still loves him. She calls Drew on his cell phone and arranges to meet him at a bar near City Hall. Drew returns home with Nicki and announces their marriage. He leaves to meet Kate before Lewis and Oswald can warn him of her intentions. She proposes to Drew, who immediately accepts. Meanwhile, Steve refuses to forgive Mimi for driving his brother insane.

Oswald, Lewis and Steve are shocked to learn that Drew is married to both Nicki and Kate. Drew intends to clear up the situation immediately, but puts it off for two weeks. He alternates between wives, telling each woman that he is away in Toledo on business when he isn't with her. Unfortunately for Drew, Mimi finds out what is going on. Drew begs her not to rat on him. He tells her that he loves both women and is abstaining from sex until he can narrow it down to just one wife. Mimi still feels that his behavior is sleazy, and tries to set him up for a fall. Kate calls while Drew is with Nicki, and he ends up having to agree to a dinner with both of them. He tells Nicki that Kate has gone crazy and thinks that she is married to him. He then tells Kate that Nicki has gotten hooked on anti-depressants. He manages to keep them at bay until Kate finds wedding cake in the freezer that says ""Drew and Nicki."" Oswald and Lewis decide to look for a house because women are turned off

Drew manages to convince Kate that Nicki made the wedding cake herself because she is crazy. He becomes desperate to clear things up as soon as possible. With Steve's help, Drew realizes that Kate is the woman he really loves. He decides that he will explain everything to her and beg for forgiveness. Before he gets a chance, Kate and Nicki figure it out on their own. They turn to Mimi to help them get revenge. She is reluctant because she wants to prove to Steve that she has changed, but gives them some advice. Drew meets Kate at the Warsaw to confess. She claims that she blames everything on Nicki, and races off to Drew's house in a rage. They stage a fight and throw a mannequin out the window onto his car. They both confront him, and an already furious Nicki leaves after learning that Drew has jilted her. He pleads with Kate for another chance, but she says that she never wants to see him again and peels out in her car.

Lord Mercer and Milan celebrate their financial success by giving the employees fancy new desks. They later learn that their accountant has cleaned them out, and have to lay off a bunch of employees. Drew, Mimi and Mr. Wick are forced into duty on the sales floor, where Drew sells underwear. When the store continues to flounder, Lord Mercer converts it into a discount outlet. Nicki sends Drew a gift and claims to have forgiven him. Drew is suspicious, but decides to meet with her. She has gained back all of her weight and is homeless. She tries to shoot Drew, but drops her gun. Drew feels responsible for her problems and offers to let her stay with him. Nicki finds a knife in the kitchen and thinks about stabbing him, but is distracted by cheese and decides that she can kill Drew later.

Drew takes in an unemployed high-school pal while jockeying for a job of his own at the newly reorganized Winfred-Louder. Meanwhile, Kate decides to drastically alter her travel plans in New York.

Drew pulls out all the stops to stop Kate from walking down the aisle with her military beau--and out of his life for good.

Recurring dreams of Kate force a heartbroken Drew to forego sleep, until Mimi offers him a surefire way to get over being dumped. Meanwhile, Lewis finds some unsettling common ground with Nicki after taking her out on a pity date.