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.

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.

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 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.

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.

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 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.

The gang tries to teach Gus to lie to an insurance adjuster so that Mimi can receive the claim on her house and be able to replace it.

After Evan leaves for a yoga retreat, Traylor begins a romance with Scott as part of a power play to seize control of the office. She puts an end to the laid-back work environment; and worst of all, takes away the foosball table! Meanwhile, Lewis gets involved with the Warsaw's new cook.

Drew hopes to make a commitment to Kellie after they learn that she is pregnant. However, she is unsure if this is the right decision. Drew seeks her parents' help to change her mind, only to find that they are not exactly thrilled with the idea of having him as their son-in-law.

Kellie is furious with Drew after he blows off an appointment to see their baby's first sonogram to go drinking with the guys.

Drew receives a letter from Steve with a check to help since Mimi lives with him. He wants back with Mimi but she is dating Larry so Drew arranges a meeting. Then a one-night stand Steve had in his world travel arrives and Steve tells Mimi.

Drew comes up with a plan to open a retro store, and seeks a partnership with the now-wealthy Wick. However, all of Wick's funds come through his father-in-law, so Drew must help cover up Wick's extra-marital affair or lose his financial backing.