Drew finds himself out of work again when Winfred-Louder goes bankrupt. The new owners convert the site to a dot com. Mimi turns to Drew for financial help after Steve loses his job at the prison. Nicki continues to live at Drew's house, where she wreaks havoc with his love life. The guys take Drew to a strip club to cheer him up. He recognizes one of the dancers as Kellie, a girl who supposedly went to high school with them. She is recently divorced and down on her luck. Drew decides that there is room for one more damsel in distress in his house and offers her a place to stay. Nicki doesn't take too kindly to this. Drew helps Kellie get a job at the Warsaw. Kate, who is vacationing in New York, repeatedly tries to call Drew. She finally comes home and says that she is getting married in two days.

Kate plans to marry Kirk, a fighter pilot whom she has only known for two weeks. They will move to Guam, where he is stationed. He has already been divorced once, and seems to have a predisposition toward cheating on his girlfriends. Drew suddenly decides that he cares about Kate again, and tries to do whatever is necessary to keep her from making a huge mistake. He locks Kate in the basement, but Nicki lets her out. Kate insists that she knows what she is doing. Drew doesn't want to attend her wedding, but shows up to give her away.

Drew is continually plagued by nightmares about Kate's wedding. He finally reaches the point where he can no longer stand to go to sleep. Mimi suggests a simple way to get over his broken heart: marrying someone else. Lewis takes Nicki on a date in the hopes restoring her confidence so that she will move out of Drew's house.

Kellie realizes that Lewis and Oswald cannot stand her because they consider her a boring goody two shoes. She tries to win them over by stealing a cardboard cutout of Indians slugger Jim Thome, but ends up on the run from the cops. Drew books a chapel for his wedding, even though there is no indication that anyone wants to marry him.

Drew convinces Kellie to make his evening out with a potential wife candidate a double date. However, she winds up jealous because she hasn't gotten over the crush she had on Drew in high school. A guilt-ridden Oswald hires a thug to rough him up after he accidentally knocks out his mother's teeth.

Drew's mother comes to town and sets him up on a blind date. Drew soon finds that the woman has a minor eccentricity: she likes to dress as a squirrel when she has sex. Mimi tries to find a way to profit after a few prescient dreams convince Oswald that he is psychic.

Drew discovers that Steve is having an affair with his hairdresser. Drew winds up having to cover for him by taking the woman to a work event, spoiling his potential romance with a co-worker. Mimi learns the truth and throws Steve out of the house.

Drew enlists a professional matchmaking service--operated by his former co-worker, Larry--in his search for a wife. The woman who comes out as his ideal match, Robin, seems terrific; but Drew just can't see himself marrying her. He later winds up falling for a woman on the bus.

Drew finds romance with Dawn, but their new relationship appears doomed because of her past. They can't find any time alone because one of her ex-boyfriends seems to turn up every few minutes.

Drew panics when the other analyst leaves the company, as he fears his bosses will discover that he doesn't know how to do his job. He hires a teenager to help improve his technical know-how. Meanwhile, Steve moves in with Lewis and Oswald. He drives them crazy with his constant crying and emotional comments as he tries to deal with the collapse of his marriage.

Drew takes salsa lessons in the hopes of learning to dance for his wedding. Kellie gets jealous when he becomes attracted to his instructor. She confesses her feelings to Mimi, who tells her to keep quiet. Drew practices dancing with Kellie and decides that he has a thing for her. He wants to tell her how he feels; but "unfortunately," he doesn't get a chance because her ex-husband, Daryl, barges in on them.

Drew tries to keep Kellie away from Daryl, who is confined to a wheelchair after an auto accident and seems to regret the mistakes he made during their marriage. However, Drew ends up looking as though as he is trying to hurt Daryl, and pushes the two closer together. He decides that it isn't the right time to confess his feelings.

After Oswald fails his nursing school exam, Drew feels bad and helps him get a job at the web site. Oswald finds a way to nearly destroy the entire business. He ends up being reassigned to a job that he (sort of) knows how to do--delivering packages. Mimi repeatedly sucks up to Traylor in an attempt to get on her good side after trying to kill her.

Drew's bosses ask him to do a live commercial for the web site during the Super Bowl broadcast. Unfortunately, Drew's nerves get the better of him whenever he has to appear on camera. His attempt to correct this leads to a disgusting mishap that is broadcast worldwide.

Larry encourages Drew to lose weight before attending one of his singles mixers. Drew winds up giving up food altogether, but his crash diet has unintended side effects--he can't stop hallucinating about turkeys!

Drew tries to improve his standing at work by taking a computer course over the summer. The gang tempts him into blowing it off to take a trip to Florida. Drew is wracked with guilt and his vacation, not surprisingly, turns out to be a disaster.

The gang takes part in a karaoke contest. Drew tries to coach Kellie before her performance, but she gets so tired of his constant interference that she dumps him. Drew winds up having to take the stage with an 11-year-old girl as his partner.

Drew falls for a bisexual, who offers him a chance at a threesome with her new girlfriend, another "old friend" of Drew's. Mimi lets Steve return home, but he fears that she will continue to punish him for having an affair.

Drew cannot afford to get a birthday present for Kellie because he has spent all of his money on an engagement ring. He learns of a condo that is available for free use for the weekend, but only for married couples. Drew mock-proposes to Kellie and asks her to pose as his wife for the weekend. Trouble arises when a man starts hitting on Kellie, leaving Drew jealous.

Drew gives Lewis his Christmas bonus, a used Rolls Royce. However, the flashy car causes Lewis to undergo a strange personality transformation, and he can no longer be bothered to hang out with his longtime friends.

Drew finds an unexpected romance after he and Speedy get involved with an animal therapy program at a hospital. He agrees to loan Speedy to a dying woman, and sufficiently impresses the woman's granddaughter. He finds the relationship may not be worth it when he learns that he may never see Speedy again. Meanwhile, Oswald tries to land a date with Traylor.

Oswald and Lewis seek revenge against Drew after they discover that he gave away their Christmas gifts--handmade mugs--to a thrift store. Drew winds up getting an unscheduled colonoscopy from a Russian veterinarian.

Oswald and Lewis put Drew's picture and phone number on Buzz Beer bottles in the hopes of landing him a wife. Much to everyone's surprise, a southern belle responds to the campaign and expresses an interest in Drew. Drew travels down south to meet the woman, Lily. They hit it off, and Drew believes he may have finally found a wife. He then discovers that she suffers from night terrors.

Drew is left bruised and battered as Lily continues to suffer from night terrors. He grows tired of the beatings, but is afraid to talk to her about her problem because he believes she would leave him.

Drew decides to propose to Lily. Mimi hopes to secure Gus's admission into an exclusive prep school by setting up Kellie with the school's headmaster.

As Drew prepares to marry Lily, his mother notes how upset Kellie seems and realizes that she has strong feelings for Drew. She believes that Drew feels the same way about Kellie. Drew and Lily go through with the wedding, but the union proves to be a brief one when they realize that they really are not right for each other. Drew winds up sharing a dance with Kellie.