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 Valentine's 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's 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.
After Doug loses some major weight, he decides to take Carrie to the same vacation spot he did 10 years ago. The only problem it wasn't Carrie he took there. So now Carrie is upset with Doug, and to add on to that they get lost in the woods and can't find their way back to their hotel.
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.
When Carrie drags Doug to her business picnic, Doug plays baseball with Carrie's fellow co-workers and Carrie's boss notices his great play out in the field. So he asks Doug to pretend to be a lawyer so he can play on their real team, which gets Carrie nervous. Arthur begins to feel uneasy around Deacon when he finds out that his ancestors had slaves.
When Carrie is having trouble getting a new job, she decides to take some time off to find herself. But Doug notices that Carrie begins to become very lazy and does not do one thing that she said she was gonna do.
It's Christmas and Arthur wants to have a Christmas card sent out with a photo of him and a few close ones, but he is having trouble finding someone to take a picture with. Carrie begins to feel extremely bored because she still has no job, but when she hears that there is an opening at Doug's IPS job she decides to try it out. When she tells Doug, he doesn't feel comfortable with the idea of Carrie on his turf.