Holly asks Doug if she can get a raise for walking Arthur, while Carrie gets a promotion on being the project supervisor which changes her hours from 8 PM to 6 AM, so now Doug and Carrie get to hardly see one another. Doug also has trouble sleeping at night so he decides to use Arthur to solve his problems.
Doug and Carrie get new neighbors who are really clean cut and high class people. When they get to know them Carrie feels that she and Doug are below them. Carrie really begins to care on what they think about them. Arthur keeps thinking of sneaky ways to convince Spence in getting into the subway for free.
Deacon brings his son over to Doug and Carrie's house after foot ball practice, and Deacon begins to complain about how Kirby hates it. So Deacon asks Doug to help him teach the team. Doug begins to love the sport again...a little to much.
Doug and Carrie go to the supermarket and pick up their developed pictures, however they get another couple's pictures and in every picture the couple is doing something exciting. This makes Carrie feel that she and Doug don't do enough with their lives. Doug does not want to do anything exiting until he picks up the couple's newest pictures again and looks at their racy photos. Arthur gets a cell phone and has no one to talk to.
Doug has to cancel dinner with Carrie on valentines day because IPS is having him deliver penguins to Albany. But he is in for a surprise when the penguins get loose in his truck. Holly just got dumped by her boyfriend and comes crying to Carrie, so Carrie tries to make her feel better by going out with Holly to a club. Arthur and Spence spend their Valentine at the local senior center.
Danny becomes an IPS driver and Doug gets upset because he feels that Danny is always following in Doug's footsteps. Doug's boss also told him to show Danny the ropes. But when Doug gives Danny his route to prove to him he cant do that well, Danny proves him wrong by completing the route 45 minutes faster then Doug. Holly tells Arthur that he is like a Grandfather to her, but Arthur wants to be more like a Dad.
Arthur reveals he has a half-brother named Skitch whom he has a house with. This makes Doug think that Arthur should move in with Skitch. The only problem is that Arthur hates Skitch and doesn't want to live there.
Doug and Carrie take a trip to Florida to visit Doug's parents. Doug finds out quite a few secrets from his childhood. Spence asks Arthur to help with the meeting of his girlfriend Denise and Spence's mom.