Doug tells Carrie that it is his tenth anniversary at IPS, but Carrie recalls that it should have been three months earlier. Concerned because of benefits, RSPs, etc. she threatens to call IPS to have the date corrected. Doug can only stop her by now owning up to why she is wrong about the date in question. The episode then flashes back to when Doug and Carrie were dating and Doug has to lie to Carrie about a job in order to further their relationship.
When Doug doesn't get invited to his new co-worker Jared's barbecue party, he tries to understand why Jared doesn't like him. Then later, Doug arranges that he and Jared go and deliver packages together on a long route. Carrie than begins to notice that none of her co-workers like her so to get the buzz going, she gives one of her co-workers an awesome make over.
Holly announces that she is moving to Manhattan with a boyfriend and won't be able to walk Arthur any longer. But Carrie begins to make Holly question on the big move. Deacon gets a sandwich named after himself at his and Doug's hangout because he made a combo of food that later became popular. Doug notices that he was actually the one that created the sandwich.
When Doug surprises Carrie to a relaxing get away to a bed and breakfast, it doesn't turn out the way he planned. For starters, it seems to be filled with a whole bunch of cats and owned by an old couple who don't know their own boundaries (and has a long-lost son who resembles Doug). Carrie then hears there is a spa hotel near by and decides she wants to escape. While Doug and Carrie are gone, Arthur invites a woman from the retirement home that he has had his eye on to seduce her.
One of their neighbors move and Doug and Carrie knew that Deacon and Kelly are looking for a place, so they ask if they want them to be their neighbors. But Deacon and Kelly don't want to live next door to Doug and Carrie. When looking at the house themselves Danny and Spence meet a beautiful Albanian woman who they then begin to fight over.
Carrie drags Doug to a karaoke bar and when he gets up on stage he is very nervous, but he starts feeling confident and sings great. When they get home Doug gets an e-mail from a woman that was at the karaoke bar. Doug is at first very flattered, but then the woman begins to send e-mails that makes Doug think that she is stalking him.
Arthur goes to visit Carrie's mothers grave and Carrie decides to go along. Doug gets a visit from his friend Ray Barone and they get in an argument on who is the more attractive between the two. They then find out that the ladies don't even notice them.
It's the Christmas season and Doug and Carrie run into their Reverand who ropes Doug into doing guard duty for the Christmas decorations at the church and he also gets Carrie into making a cake for the church. When Doug sees a fellow guarder's wife bring him hot soup to help warm him from the outside cold, Doug begins to feel that Carrie doesn't do enough wife stuff . Arthur and Spence decide to try and write a Christmas song.
Carrie wants a promotion at her work, but her boss says the committee won't hire her because of the way she talks. An upset Carrie decides to get diction lessons from Spence, to learn how to speak more lady like. Doug's mother comes up to visit and sits in on a guys gambling game. Doug begins to notice that she can really play so he invites her in on more games to cash in on more money.
Doug and his friends get an apartment above a Chinese restaurant in order to be away from the women in their lives. Carrie takes on Kirstie Alley as a client but soon finds out she has to be a designated "eater": for her. After a botched delivery by Doug (who takes on a job at the restaurant to pay the rent) Carrie finds out about the apartment.
When Arthur comes home from his vacation, he brings Doug and Carrie a set of sheets as a souvenir and he brings some bed bugs along too. Carrie and Doug then have to have an exterminator take care of them and he said it will take all night. So now they have to spend the night out in the city where a lot happens. Spence and Danny argue on where they want to take a vacation. Danny wants to go to Vegas, while Spence wants to go to the Aztec Ruins. So to settle there argument they wrestle for it.
It's Doug's 40th birthday and when Carrie's co-worker begins to question Carrie on whether Doug is freaking out or not about getting older and not accomplishing a whole lot. Carrie then begins to try to make Doug realize that he should start wanting to do more with his life. So Doug decides he wants to ride a roller coaster that he was to afraid to ride when he was younger.
When going to the cinema, Doug and Carrie can't decide on which film they want to see. They run into Deacon and Kelly and it turns out Kelly wants to see the picture Doug wants to see and Deacon likes the film Carrie likes. It turns out Doug and Kelly have more in common and they start doing more things together. So do Deacon and Carrie.
Carrie has to go build houses in Hartford for work while Doug wants to watch Planet of the Apes all weekend with her. He follows her to Harford and finds out she had a change of plans that didn't involve him. Meanwhile Danny and Spence find a way to sneak into a Huey Lewis concert, but things don't go well.
Carrie's work has her mentor a troubled teen, but when actually hanging out with the teen, Carrie begins to become more pressured into her old misbehaving self. Another packaging company named Priority Plus takes the IPS table at Doug's hangout and the IPS drivers let them know how much they hate them. But Doug later befriends one of them and he tries to keep the relationship secret.
Arthur accidentally starts a fire in Doug and Carrie's basement, so Carrie then begins to think that her and Doug should find him a retirement home to go live in. When Doug starts to clean out the basement by removing Arthur's things, Doug sees that Arthur used to be an actor and he finds out that he gave up the career for Carrie. This gives Doug second thoughts on giving Arthur the boot. It's Danny and Spence's two year anniversary and Spence reminds Danny on the bet they had on Spence getting the bigger room, but Danny is willing to fight him over it.