When Carrie's father Arthur burns his house down, she and Doug let him stay in their house. If Arthur wants to live in their house, Doug has to give up his downstairs paradise. Carrie's sister Sarah also moves in with them.
When Carrie keeps skipping softball games with Doug and the guys, Doug wonders what's going on. Doug finds out that Carrie is working late for her boss. Doug starts to wonder why Carrie fell for him. Doug tries to make it up to Carrie by going to a cello concert with her.
Doug and Carrie throw a wedding anniversary party for themselves. Doug invites his aunt, and finds out that his aunt and uncle are having problems. When Arthur meets Doug's aunt, he falls for her. Can Doug stop their relationship, or let it be.
When Carrie and Doug cash in her wedding ring, they wonder if they did the right thing. They buy a satellite dish and a hot tub with the money they got with the ring. They soon find out that they get bad karma from the selling of the ring. Did selling their most prized possession give them their bad karma?
Carrie decides that she and Doug are getting dumber everyday, so she signs them up for a classic literature class. Doug is not very happy about the decision, and tends to goof off in the class. They are given an assignment to read the novel "Jane Eyre", and then answer questions on what they read. Doug never reads the the book, and is desperate for the answers.
While Doug is taking a driving test, he runs into Ray Barone. Ray seems to have trouble with a few of the questions, and asks Doug for the answers. Doug is caught by the instructor, and loses his license. Ray makes it up to Doug by bringing him to a New York Jets game. Ray's brother Robert goes with them. Ray lets Doug drive, and Robert finds out that Doug does not have a license. Robert, being a cop, tells Doug to pull over. Doug finally gets his license back. Look for an appearance from Peter Boyle play Ray's father Frank Barone.
Doug is planning to take Carrie out to dinner on Valentine's Day. Before he takes Carrie out, Doug, Deacon, and Richie go to Spence's house to wish him a happy birthday. Spence's mom is throwing the party, and has had a little too much to drink that night. Spence's mom embarrasses him so much he leaves. The boys can not leave because Spence's mom is very unstable. In the mean time, Carrie has dinner with a man she met at the restaurant's bar. Can Doug make it out in time?
Carrie gets a ticket and since it's her fourth, the car insurance will be doubled. Doug is cross with Carrie about this and when the cop who gave Carrie the ticket wants to go out with her, Doug insists she goes out with him.