Doug, feeling underappreciated at work, hears that drivers at FedEx are making twice what he makes. When he runs into a former co-worker now working for the big overnight service, he takes his friend's casual banter to mean that FedEx wants to hire him. Doug uses this information to play hardball with his supervisor and instead of getting a raise and a better delivery route, he gets fired. Meanwhile, after Lou Ferrigno asks Carrie to smear his body with tanning cream while his wife is on vacation, she gets addicted to the stuff and overuses the it on her face, dramatically darkening her skin.

Doug's Uncle Stu asks him to get his son, Danny, a job at IPS. Doug doesn't want him working there but he doesn't want to look bad to the family so he instructs his boss to interview him but not hire him. Eventually, Doug feels guilty and goes back to O'Boyle to ask him to reconsider Danny for the job. Meanwhile, Arthur fills out audience comment cards on a new movie.

Carrie discovers that she is pregnant and she is panicked that the timing is all-wrong. Meanwhile, Deacon and Kelly begin to reconcile and Spence is left out in the cold and Arthur insists that Doug build him his own bathroom in the basement.

As Doug is about to break what was once thought of as an unbeatable record, the tension between he and the guys at IPS mounts. For 18 years, Iggy Stenkowski's record of 951 consecutive perfect delivery days has remained intact, and the guys resent Doug as he's about to beat it and replace the legendary Iggy's plaque with one of his own. As he deals with his internal conflict, Carrie has trouble dealing with the fact that Holly, the dog walker, actually enjoys spending time with Arthur. She starts to wonder if her father really is as great as Holly thinks he is and that maybe she's the problem in their relationship.

Carrie has decided that she and Doug don't spend enough time celebrating the good things in their relationship, and plans a night of romance in honor of the anniversary of their first date. It happens to be on the same weekend that Deacon has planned a group trip to Atlantic City, and he wants Doug and Carrie to join he and Kelly and some buddies from work. But while checking in to the hotel, Doug and Carrie find out that everyone in the group has cancelled and the only person joining them is Doug's boss, O'Boyle. Deacon shows up later that weekend and confesses that after he and Kelly got into a fight, she packed up the kids and left him.

Doug starts to dream more seriously about running his own sandwich shop now that his Uncle Stu has generously offered him a large sum of money to see him realize his dream. However, Carrie has major reservations about this, knowing that Doug's gifts are not in running a business. Not to mention that Danny, Stu's son, is very jealous and angry that his own father would back Doug's business venture, but not his own.

Doug's parents visit while Carrie's on a business trip and take over running the house, making Doug feel like a kid again. Also, Arthur tries to strike it rich by inventing a new type of screwdriver called "the Arthur's head."

Danny asks Doug for a letter of recommendation at IPS so he can move up to being a driver like Doug. Since this idea does not appeal to Doug, Carrie decides she will write the letter and have Doug sign it. Danny ends up getting the job and puts Doug's skills to the test, and his job on the line, when his ability to beat Doug's delivery time has the boss giving Danny Doug's route.

Carrie hears that her law firm is laying off people and worries about her job, though her resigning boss is only worried about getting an omelette bar goodbye party. Meanwhile, Doug is in hot water with Deacon when he loses the koosh ball Deacon received from his son as a gift.

When Arthur tries to sell Spence his adjoining burial plot, he somehow winds up selling it to Spence's mother, Veronica. Doug is assigned a new delivery route and is freaked out by a man at one of his daily stops who always answers the door wearing nothing but a towel around his waist. Meanwhile, Carrie takes on dog walking with Holly to make some money after being unemployed for several months, but immediately hates the job and hires a kid to do the walking for her.

Carrie and Doug have a conflict of interest when Carrie begins to stay late every night at work but it leaves Doug to feel neglected.

As the snow falls in Queens, Carrie heads out to buy an iPod - but instead of achieving musical nirvana, she finds herself stranded on a cold street and in a moral dilemma. Meanwhile, when a couple invites Doug in from the cold, he manages to quickly use up his welcome when he dispenses very un-welcome relationship advice.

Carrie finds out that while dating, Doug lied about getting a job to get her to sleep with him.

Doug and Carrie both have feelings of not being entirely popular at their workplaces, and both overcompensate to rectify the situation

Doug's lie to get Carrie to let him ride a rollercoaster at an amusement park blows up in his face. Meanwhile, Arthur lets Deacon shuttle him around in a wheelchair so they can jump to the front of the park's lines and Danny and Spence search for girls to pick up.

Doug and Deacon fill in for Supervisor O'Boyle at the IPS depot. Carrie regrets her decision to complain about her company's chinzy gift for work on an important project.