After Deacon and Kelly's separation, Carrie begins to wonder about her own marriage. She and Doug agree to put their sex lives on hold for a few weeks because Carrie feels that they should resolve arguments verbally, not always physically. Meanwhile, Arthur dates a woman who claims she was once Frank Sinatra's girlfriend.

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 is invited to her company's retreat for the first time and is overcome with excitement. Doug is not so thrilled, however, when he discovers that he must spend the whole weekend sans TV. While away, Carrie mingles with the other lawyers and partners while Doug stands by very uncomfortably. Doug then tries his best to charm the partners and in his effort ends up in a lie about climbing Mount Everest – much to the delight of Carrie who sees this as an opportunity to advance herself at work. Meanwhile Arthur, all alone at home in Queens, ends up destroying Doug and Carrie's bedroom and begs Deacon to help him hide the damage before they return home.

Doug decides to buy a pumpkin to get into the Halloween spirit, but as soon as Arthur sees it, he smashes it and banishes the celebration of Halloween. Doug, frustrated by Arthur "forbidding" things, takes it upon himself to go all out with decorations and ends up scaring Arthur so badly that he nearly has a heart attack and ends up in the hospital. When Doug finds out about Arthur's traumatic childhood and the reasons why he hates Halloween, he feels guilty for what he has done and tries to make it up to him by driving around town, looking for Arthur's favorite childhood treat. Deacon, on the other hand, is determined to find his son Kirby a superhero costume, but is frustrated because there aren't any black superheroes. Deacon resigns himself to the fact that Kirby is gay because he turns down the Darth Vader costume so he can be a Power Puff Girl.

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."

When Carrie's new afterwork routine of apple martinis-along with an accompanying much more relaxed attitude-come to an abrupt end, Doug and Arthur join forces to keep her drunk, a course of action Lou doesn't approve of.

Carrie and Doug begin preparing for tax time and realize that their charitable giving leaves a little to be desired. In an effort to get out of feeling guilty and to make amends for what they see as "selfish living" in the past year, they decide to make a donation to the local kid's library at Deacon's son's school. However, Carrie's charitable spirit starts to be about recognition rather than the actual joy of giving. When the administration mistakenly thinks the Heffernans gave $500 rather than $50, Doug and Carrie scramble to keep the recognition without having to pay the price.

Doug and Carrie are having fun on their vacation with their neighbors in St. Croix, but once Arthur calls with a quote on the current mold problem in the house, all is not so fun.

The mold problem in the Heffernan household grows and Doug and Carrie find out to fix the problem will cost them $12,000! Doug, with his tail between his legs, goes to his father to ask for the money, but hits a wall when he wants to know why he and Carrie don't have it in the bank. When Doug has to admit they have no savings, his dad wants to comb through their financial books to see where all the money is going. This prompts Doug to limit Carrie on her "wild spending," which does not go over well with her.

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 can't stop buying expensive clothes, and then returning them within a few days. Spence's new girlfriend is afraid of his dog and tells him to decide who he wants, the dog or her.

Arthur and his half-brother Skitch are reunited when Doug sets it up for them to meet again at the tollbooth Skitch works at on the freeway. When Doug realizes they own a house together, he sees the possibility of getting his personal life back when he envisions the basement empty and he and Carrie having some personal time. Arthur moves in with Skitch until all hell breaks loose when the two are reminded that they should indeed live apart.