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.

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 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.

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 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.

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 is thrilled when he and Kellie decide to exchange keys. However, he nearly thwarts the progress in their relationship when he ends up letting Scott use Kellie's place to cheat on Traylor.

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.

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.