Doug and Carrie decide they want to have a baby, but Arthur keeps getting in the way. Now that his last friend moved away he has nothing to do all day, so he bugs them at night. Doug decides to hire a dog walker to walk Arthur so he can spend time with Carrie.
Doug realizes that Carrie has hated every gift he has given her. When she starts having to wear glasses again because her vision is going, he decides to get her laser eye surgery. But the problems come when Carrie ends up blind.
Doug is close to beating the record for most perfect delivery days. As he nears the 951 day record the people he works with start to get jealous.
Doug and Carrie get in a fender bender with Deacon and Kelly, and the agreement for Doug and Carrie to pay for the damages to Deacon and Kelly's car causes problems between the two couples. Meanwhile, Spence babysits Deacon and Kelly's son, Kirby, who, not understanding what "allergic" means, believes Spence to be afraid of peanuts and stops calling him the "Spencinator," referring to him as the "Scaredinator" instead.
Carrie and Doug go to her company's retreat, and Carrie, hoping to impress the firm's partners, encourages Doug to be friendly with them, which Doug finds difficult. Meanwhile, Arthur is left at home alone, and Deacon has been instructed to check up on him.
Arthur forbids Halloween to be celebrated in the house, and Doug, fed up with Arthur's demands, defiantly decorates the house with Halloween decorations, which scares Arthur into the hospital. Once Doug finds out why Arthur hates Halloween, he attempts to find a way to make his father-in-law feel better, which is more difficult than he initially thought. Meanwhile, Deacon is concerned with his son's choice of Halloween costume.
As Arthur is about to have his surgery he asks Carrie to bring him his sleep mask. When she is digging through his stuff looking for it she finds an old letter from Florida State saying she got into college. She never saw the letter before and starts to resent her father.
After the surgery, Carrie decides it would be a good idea to get life insurance and to make sure Arthur has somewhere to go if one of them dies. When she finds out Doug wouldn't want him if she dies she gets upset. She starts smoking again and Doug thinks she is trying to die first.
When Carrie is cleaning out the freezer she finds part of their wedding cake and Doug and Carrie reflect back to their wedding day.
When Doug's first instinct is to use an oxygen mask - released accidentally during a plane landing - for himself instead of allowing Carrie to use it, she is upset, and he tries to prove that he would be willing to risk his life to save her. Spence looks for a new place to live when his rent is raised again and is surprised when Danny doesn't want to live with him.
Carrie's boss gets his first big case and he needs an expert witness from IPS. When he asks Carrie to get her husband, she is worried he might embarrass her so she goes back and forth having Deacon and Doug come.
Doug's parents come over for Christmas. Carrie is ovulating and they want to use this time to get pregnant, but Doug's parents are getting in the way.
Carrie gets jealous when Doug starts paying a lot of attention to Spence's girlfriend, Becky. She is a great cook and Doug is always talking about her food. Carrie tries to impress Doug with her cooking, but can't do it.
Carrie wants to spend a weekend with Doug to honor their first date, but it is the same day as a trip Deacon planned to Atlantic City with a group of friends. Carrie agrees to go but the only other person who shows up is Doug's boss. Deacon shows up later and says Kelly left him and took the kids.
Doug decides to take Deacon out to find women after Kelly left him. When he gets to the club he realizes how much he misses them and starts going even when Deacon doesn't come.
Carrie finds an unopened gravy boat that they got from Doug's third cousin Ron and his wife Marcia at their wedding. It has a check for $1,500 in it but it is too old to cash. When they invite them over and get a new check, Doug says how they were thinking of going to New Orleans, and Ron and Marcia want to go too. But Doug hates them and they go without Ron and Marcia, but Doug can't relax knowing they are doing this. Arthur decides he wants to create a comic strip for Playboy magazine and hires Spence to draw it for him.
Doug and Carrie get tickets to the annual golf outing Carrie's law firm has. They normally take Deacon and Kelly, but they can't. So Doug finds Deacon a new girl, but Carrie hates her.
Doug's uncle offers to fund a sandwich shop for Doug which has always been his dream. Carrie thinks it is a bad idea and has to find a way to stop Doug.
Carrie is out of town and Doug's parents are over. Doug has to take a test for IPS to make sure he is a safe driver and decides not to study, but he fails and soon his mother starts running his life. Arthur creates the Arthur's head screwdriver to try to get rich after a conversation with Doug's father.
Carrie has started going out for drinks after work with her friends and is coming home nicer than usual. When she gets in a fight with them, Doug realizes it is over, so he starts giving her alcohol at home to make her happier.
Carrie has started wearing her hair in a bun, which is driving Doug crazy. His high school reunion is coming up and he wants her to go back to her old look so she doesn't look like a librarian.
Carrie and Doug realize they haven't been very charitable in their life so they give money to Deacon's son's school. When they are credited as giving less than they gave, they wonder if they should speak up.
Doug takes $100 from the emergency fund jar to bet on boxing, and wins $5000 with Deacon. But they realize they can't tell anybody or Carrie will know he took the money, and Kelly will try to get the money in the divorce. They decide the best thing to do is blow all the money on the best day ever.
Doug visits a dentist who used to like Carrie, and Doug thinks that he is hurting him on purpose for getting Carrie. Arthur owes Deacon some money so he decides to teach Kirby to play piano, even though he has no idea how.
Arthur goes to visit a psychiatrist and they discover what may have caused Arthur's unique personality.