Doug becomes a Big Brother. Which leads him to running a 10K race to support heart disease; Carrie accidentally tells another Doug she loves him.

Arthur begins to work at Carrie's company; Doug and Deacon compete for the best practical joke.

A battle of who got the cheaper gift begins; Lou Ferrigno moves next door.

Doug sets up his sister with Carrie's boss so that he can watch the Super Bowl on a high-definition TV.

Doug and Carrie meet the neighbors after a hurricane destroys both of their backyards. Carrie breaks their hearts by telling the truth and rejects the idea of a combined backyard. So the neighbors retaliate by disrupting their privacy by making an aboveground pool in a small space. But as Carrie tries to mount a lawsuit, Doug can't deny the temptation and joins the other side. But before the pool goes down, Carrie takes a quick swim and later, Doug tries to enjoy the lawn sprinkler.

Doug thinks he has come up with the perfect birthday gift for Carrie: laser eye surgery. That is until Carrie ends up nearly blind from the operation.

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.

Carrie's boss, Pruzan, has his first big case as partner, and Carrie is overwhelmed with work. To complicate matters more, the case involves testimony from a delivery driver and Pruzan wants Doug to be the expert witness because he drives for IPS. Although Doug is really excited about working with Carrie, she isn't as thrilled with the idea. After Doug shows up to get prepped for the trial, Carrie is panicked that he is going to embarrass himself and her, so she tries to get Deacon to testify instead, which of course, hurts Doug's feelings. Pruzan is insistent that Doug be the witness, and after a lot of begging from Carrie, he agrees to come back and help her out. Over in Danny and Spence's apartment, a feud has ensued over Holly, the dog walker. Their strategy on getting the girl by spending the entire day with her backfires when she ends up giving her number to the gas man that comes over to fix their heater.

Now that Deacon and Kelly have separated, Doug makes it his mission to get his friend out of the funk he's been in by taking him out to the clubs. Doug starts to realize he's been missing the days of hanging out with the singles and starts making a habit of it. In the meantime, Carrie is threatened by the new office assistant at the firm, Lila, who has an uncanny resemblance to her. The constant comments from the people at work starts to drive Carrie crazy and she decides to change her look a little in order to stop the comparisons.

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 cannot spend time with Carrie on Valentines Day, because he has to deliver penguins, with Deacon, from one zoo to another. Yet, along the way, they run into some mishaps. Meanwhile, Carrie and Holly go out and give her tips with men to look for a man for Hall. However, Carrie inadvertently fixes her up with her boss. Also when Arthur and Spence go to up a pick a date for the holiday, he accidentally gets himself a date that is old enough to be his grandmother.

During a romantic dinner, Doug is inspired to proclaim his love to Carrie. Carrie is taken by his gesture and suggests that they renew their vows. The two find that planning the wedding is much more troublesome than expected. The ceremony is on again, off again as Doug and Carrie are faced with endless complications, including finding a chimp to serve as Doug's best man. In the midst of the wedding planning Arthur is praying that his wedding present, aged Port wine, will go unused when he discovers the value of the fine wine on E-bay.

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.