Against Carrie's commands, Doug takes $100 from the "emergency fund jar" to bet on a boxing match. When he and Deacon win $5,000, Doug realizes he can't let Carrie know he won big or she'll realize he stole the money. Deacon and Doug set out to burn it all off in a day of luxury spending. Meanwhile, Carrie is offered a job from the owner of the firm and when she finally works up the nerve to give notice, the offer ends up not being as firm as she thought.moreless
When Carrie suggests life insurance, Doug worries she could die, leaving him to take care of Arthur. Deacon, Spence, and Danny enjoy watching Arthur's mundane daily activity via a camera Doug installs.
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.
As his high school reunion approaches, Doug worries that Carrie's new hairdo will make her look like a librarian, rather than his usually sexy wife. Hoping to show Carrie off in front of his former classmates, Doug tries to find a way to tell her that he hates her bun without hurting her feelings. Meanwhile, Spence informs the guys that he's nervous about seeing one of his old teachers because he never called her back after the two shared an intimate encounter.moreless
Coming across the top tier from her and Doug's wedding cake sends Carrie reminiscing about their wedding day, including desperately wanting to find a sign that she's meant to be with Doug, Arthur tricking Doug's parents into paying for the wedding, and Danny wanting to sing.
Doug's distraught when a weekend with Carrie at her company's retreat is lacking television. 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.
As Arthur prepares to undergo heart surgery, he asks Carrie and Doug to bring him his sleep mask, and she makes some interesting discoveries while looking for it. Meanwhile, Doug makes friends with a quirky stranger in the hospital and soon regrets it.
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.moreless
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."
Doug rear-ends Kelly and Deacon's car, and he and Carrie insist that they personally pay for the damage so they can leave the insurance company out of it, but the estimate leads to a rift between the families. Meanwhile, Spence is babysitting Kirby and goes from being the "Spencinator" to the "Scaredinator" once Kirby finds out that he is allergic to peanuts.moreless
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