Doug learns a secret about Richie's wife after a disastrous dinner party.

Doug helps a sportswriter cheat on the driver's exam.

Carrie fixes up Spence with a co-worker, and everything is going fine until Doug offers Spence some advice on the relationship.

When the shift supervisor leaves for heart surgery, Doug is selected for the position, but despite the promotion, he hates the job. On top of that, Deacon feels he was overlooked because he's black.

Carrie asks Doug to join her at a dinner party for a Japanese client. But when he arrives ravenous after not eating all day, he discovers there's no dinner and tries to eat whatever he can find.

Doug and Carrie, along with Deacon and Kelly, go on a weekend trip. While there, they find out that Deacon and Kelly have a very active sex life.

Doug has his old football teammates over; Meanwhile, Spence tries to get his revenge on the football players for what they did to him in high school.

Doug loses a lot of money when he and Deacon go to Atlantic City to gamble.

Doug gets pulled into a water filter scheme thanks to his neighbors.

Carrie has Doug sign a congratulatory card for his boss' twenty years at the company and the whole thing blows up in Doug's face. Now, Fisker, the boss, wants Doug to participate in the banquet roast and Doug blames Carrie for this fiasco. He does rise to the occasion, however, and even manages to get some good laughs out of the audience. That is, until he starts to tell some jokes that hit a little too close to home.

Doug becomes jealous when Carrie makes the mistake of telling him she finds Deacon attractive; The gang go paintballing to celebrate Deacon's birthday, which turns into a war of jealousy.

Doug is surprised to find his married best friend, Deacon, out with another woman. Meanwhile, Carrie questions her relationship with Doug because of their different views on cheating.

Doug's Uncle Stu asks him to get his son, Danny, a job at IPS. Doug doesn't want him working there but he doesn't want to look bad to the family so he instructs his boss to interview him but not hire him. Eventually, Doug feels guilty and goes back to O'Boyle to ask him to reconsider Danny for the job. Meanwhile, Arthur fills out audience comment cards on a new movie.

As Doug and Carrie's plane makes an unexpectedly rough landing, Doug takes the only available oxygen mask for himself and doesn't think twice about Carrie. She is hurt that he would think of himself first, while he doesn't think that he's done anything wrong. It's not until Carrie says that she will forever see him differently that Doug feels guilty for what he did and tries to prove to her that if her life were in danger, he would save her. Meanwhile, Spence needs to find a new place to live and ends up moving in with Danny Heffernan after things with the hot Brazilian exchange student don't go as he'd hoped.

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.

Carrie has been put in charge of overseeing a group of people who will be organizing and distributing legal documents for one of her firm's big cases. The catch is that her team will have to work the night shift, and they're "not the sharpest tools in the shed." Doug is disappointed by her new appointment because this means that they won't be spending any time together, but then decides to use her time away as an opportunity to do whatever he wants – eat in bed, not brush his teeth before he goes to sleep, etc. Unfortunately, he starts to get a little lonely but soon discovers that Arthur makes a suitable companion to keep him company.

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.

Since Doug never gets what he wants from Carrie, he uses Arthur to ask Carrie for them, so he gets what he wants. Meanwhile, Spence is first on line to see a new movie.

When Arthur handily beats Doug in several games of ping-pong, Doug decides to test his skills on Carrie, but is humiliated when he loses once again. In a desperate attempt to keep his ego intact, he asks Arthur to train him so that he can beat his wife. Meanwhile, Spence's girlfriend, Denise, gets promoted to waitress at the bowling alley, but Spence becomes jealous of the flirting she must do to get tips.

After countless times of babysitting Deacon and Kelly's children, Doug and Carrie feel that Deacon and Kelly should return the favor and babysit Arthur every once in a while. Deacon and Kelly decide to take Arthur out to dinner so Doug and Carrie can be alone, but they ignore a warning about Arthur's reaction to spicy food.

What starts out as a valiant effort to win back the heart of Spence's ex-girlfriend, Denise, quickly goes south as Danny gets a sudden case of lockjaw and the group spends all the money they took out as cash advances from their credit cards. To Carrie's dismay, she can't buy groceries because unbeknownst to her their credit card has been maxed out by Doug. Meanwhile, Arthur fills in at the front desk of the senior center and has some words with the pudding vendor.

Carrie and Doug have a conflict of interest when Carrie begins to stay late every night at work but it leaves Doug to feel neglected.

Carrie uses her extra income to hire a maid, but Doug feels left out and decides to hire his own help in the form of Spence's mom, Veronica. Soon, Veronica proves to make more messes than she cleans, especially when her newly subordinate position makes Arthur pine for her.