Doug and Carrie try desperately to ship Arthur off to friends for the weekend so they can enjoy some intimate time together, but no one's eager to take him.

Carrie convinces Doug to be the best man at his cousin's wedding.

Doug lies to Carrie about having to work late so he can play mud football and get out of going to her seminar. Now sick from his night of football in the rain, Doug starts watching TV and begins to drift off to sleep... Doug, finally full of guilt, goes to tell Carrie the truth of what happened and she doesn't react exactly the way he thought she would.

Doug feels sorry for Arthur and agrees to let him go to a cocktail lounge instead of to the weekly dance at a senior center. When Carrie finds out, she goes ballistic and turns her father's care over to Doug-a job he soon regrets taking on.

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.

Deacon asks Doug to help him coach his 8-year-old son's football team and the boy challenges Doug to try out for a semi-pro team, but Carrie isn't thrilled with the idea until she sees an interesting photo of him.

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.