Carrie discovers a romantic line Doug once said when they were dating comes from a film where the main character said it to a monkey. Meanwhile, Danny falls for Holly and thinks she feels the same way about him.
It's Arthurs birthday and to avoid spending time with Arthur, Doug calls himself on his own cell phone and acts like he has to report to work. But when Carrie finds out that Arthur's birthday wish is to spend more time with Doug, she tries to force Doug on having more bonding time by him taking Arthur to St. Louis for the College Baskeball Final Four. While Doug and Arthur are gone, Doug's dad stops by unexpectedly and Carrie is forced to spend some bonding time with him.
When Carrie has to take a trip to Lowes because she is re-doing her office, she asks Holly to come along because Holly has more room in her van. Carrie tells her the reason she wanted her to go is because she thinks that Holly has good taste, but she and Holly have opposite tastes. Doug tries out a new diner, but the waitress ignores him which causes problems and the waitress then wants to fight Doug. Arthur wants to go on a senior cruise so to get the money he starts to do a little gambling with other senior citizens.
There's a blizzard in Queens so Carrie hurries to buy herself an I-pod, but when the clerk doesn't ring the iPod correctly, Carrie complains and gets the clerk fired and gets a free iPod. When her car gets stuck in front of a church, she begins to feel guilty. Doug is out in the storm delivering, but he stays at a nice couple's house until the storm passes. Arthur stays at Holly's while she has a date come over.
When Doug finds out that he can earn a free Plasma screen TV at a timeshare ski resort, he tricks Carrie into going. But they both find out it will be difficult in getting that TV when the sales people enter the picture.
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 Reverend 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.