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.

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.

Doug's bowling team prepares for a tournament, while Carrie agrees to babysit Mr. Kaplan's son, in hopes of furthering her career. But when Doug throws out a mercy flirt and Carrie runs into an awkward set of hands, all goes downhill.

When the partners of Carrie's law firm notice Doug's softball skills, they ask him to pretend that he's a lawyer in order to play on their company team. Carrie worries that Doug won't be able to pull off being a lawyer, but he is so convincing, an opposing firm offers him a job. Meanwhile, after tracing his ancestry, Arthur believes his great-grandfather was a slave owner and makes it his own personal mission to correct things with Deacon on his ancestor's behalf.

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.

Doug decides to spend the Heffernans' tax refund on an ice cream truck. Meanwhile, Carrie fills in as a pretend mom at model homes, and discovers a reemergence of her maternal desires.

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.

Carrie soon grows tired of Doug's forcing his new vegetarian lifestyle down her throat. Meanwhile, Carrie's boss wants to start discussing novels with her and Spence takes on some humiliating new jobs.