After Holly gets kicked out of her apartment, Arthur insists that she stay with him in the basement until she finds a new place, making Doug realize the benefits of having two women in his life.

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.

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.

It's Thanksgiving in the Heffernan household and while Carrie cooks dinner for ten people, Doug lets a stranger into the house to use the phone. He is convinced the stranger is a nice guy but Carrie is not so trusting. Everyone at dinner feels sorry for the man, who's been left outside to wait for a ride, but when Carrie finally gives into the holiday spirit, it turns out her instincts may have been right.

Doug must heal the breach between father and daughter when Arthur ruins Carrie's job interview at a prestigious real-estate development firm by making a nuisance of himself in the company's lobby.

When Doug hears from Carrie that Deacon's ex-wife wants to reunite with him after a two-year separation, he can't decide whether or not to give Deacon the heads-up. When Deacon informs Doug that he just met a beautiful stewardess and is spending the entire weekend with her, Doug decides not to tell him about his ex-wife's plans to reunite with him. But when Carrie discovers this, she demands that Doug tell Deacon so he doesn't ruin his chances of getting back with Kelly.

Doug sabotages Carrie's attempts to start hanging out with her co-workers by scaring them off with several crude techniques. Meanwhile, Spence and Danny realize that women like men who take care of the elderly and start using Arthur as bait.

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.

In flashbacks, Doug and Carrie recall buying their house almost 10 years earlier and how it was mainly Carrie's decision because Doug preferred a different place.

Doug surprises Carrie with a romantic weekend away at a resort. Doug and Carrie try to get over an argument they've been having, but only make things worse. Deacon finds Spence and Danny in bed together. Arthur decides he is in an emergency situation.

Doug and Carrie run into Doug's ex-girlfriend Trish at an art gallery. Doug explains to his wife that Trish took their breakup pretty hard. So, against her husband's wishes, Carrie asks Trish out to lunch. At the restaurant, Carrie quickly realizes why Doug broke up with the woman in the first place – she's annoying and needy. Ready to break off their new friendship, Carrie's tune changes when she discovers Trish's employee discount at Saks Fifth Avenue. Meanwhile, Spence agrees to go out with a guy, even though he's not gay, just to boost his morale.

When Arthur tries to sell Spence his adjoining burial plot, he somehow winds up selling it to Spence's mother, Veronica. Doug is assigned a new delivery route and is freaked out by a man at one of his daily stops who always answers the door wearing nothing but a towel around his waist. Meanwhile, Carrie takes on dog walking with Holly to make some money after being unemployed for several months, but immediately hates the job and hires a kid to do the walking for her.

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.

A bedridden Carrie gets Doug to team with Arthur for a shuffleboard tournament, but his skills aren't to Arthur's liking. Meanwhile, Carrie pretends to continue being sick so that Holly will continue to cook for her.

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 finds it unbearable working with Carrie when she takes a temporary job at his company during the holidays. Arthur tries to get various friends to pose for a Christmas card picture with him.

Arthur wins $2,500 at a bingo game, and agrees to share some of his winnings with Doug and Carrie. Unfortunately, Arthur feels that he should decide how they will spend their portion.

Doug and Deacon's relationship hits a speed bump when Deacon unknowingly befriends Doug's grade school archenemy.

The sixth season opens with a newly svelte Doug and a surprisingly jealous Carrie, who just can't hide her disdain when people constantly compliment her hubby on his weight loss. Doug decides to suprise her by taking her to an old holiday spot of theirs.

Carrie fears that her new gynecologist will drop her as a patient after she recommends Danny do some landscaping for him and Danny overcharges the doctor for the work.

Doug gets annoyed with Carrie when she loses her job and, rather than looking for employment, becomes extremely unmotivated. When Doug confronts Carrie about her laziness, she gets upset, claiming that she is simply trying to find herself. Carrie then enlists the help of Arthur and opens up her own company making decorative cell phone covers. However, when she invites her friends over to buy some of the covers, she realizes a new line of work might be in order.

Carrie becomes furious with Doug after he is hospitalized to remove his appendix and begins talking about other women while sedated. To ease the situation, she writes a list of acceptable fantasies – and women – for Doug to dream about.

Carrie asks Deacon and Kelly to accompany her and Doug to Florida for their visit with the in-laws so that they'll be forced to stay at a hotel instead of with Doug's parents. What looks like a perfect vacation turns into a nightmare when spring breakers invade the hotel, forcing Carrie and Doug to reconsider their future accommodations when visiting the folks. Adding to the misery is the great disappointment shown by Doug's mom over the fact that no one is staying at her house.

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.