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 their 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.
When Doug wants to buy a chainsaw, Carrie reminds him that when she says "No" about something Doug can't argue on it because of the first house that he got when he and Carrie first married. It was a complete disaster.