Dana needs to buy a new car and Cheryl offers to go with her, but Jim says chicks are no good buying cars by themselves, because they'll get distracted with other less important things like mirrors or cup holders. Offended, Cheryl is determined to prove Jim wrong and actually gets Dana a car for a fair deal, but the car soon breaks down. Jim takes over the situation and goes down the dealership to manly handle the situation and deal with the salesman. The only thing he wasn't counting on was a very seductive female manager, who convinces Jim to trade in his minivan ...
Jim and Cheryl have a new house guest when the pizza delivery boy moves in with them. Ronnie wants to do stand up comedy, but his father tells him he will never make money that way. Ronnie decides to move out of his father's house.
Jim takes the girls to their first baseball game, and Cheryl tells him to be on his best behavior and set a good example. At the game, Jim gets into a shouting match with another fan, and their argument ends up on the show broadcast.
Dana gets accepted to be on the reality show The Bachelor. Jim gives her advice on how to keep a man interested. When Dana and the bachelor visits Jim and Cheryl for dinner, the bachelor reveals to Jim he only wants to get Dana in bed.
Cheryl and Jim are organizing the school's Thanksgiving Day play, and when they are alone on the set, they decide to get intimate. Andy and the PTA President walk in on them, and the story gets spread. Cheryl is dismissed from the play.
Cheryl has to do everything to prepare for Ruby's birthday party since Jim seems to mess things up. On the day of the party, Jim ends up having to deal with all the little girls for the sleep over party.
Cheryl needs a root canal, but she does not want to have it done. Jim says he will go with Cheryl so she will have support. However, at the dentist office, Jim realizes that Bo Diddley is in the building and he wants to leave Cheryl.
Cherly's new friend is another soccer mom who Jim finds annoying. Cheryl enjoys her company, so the two families become social friends. Eventually, Jim tells Cheryl she has to break off the friendship.
Dana takes Ruby to the park, and a single father strikes up a conversation with her. When Dana realizes he thinks she is the mother of Ruby, she decides to keep up the charade. Cheryl asks Jim to exercise more.
Cheryl's mother comes to visit, and tells everyone she is engaged. Cheryl and Dana are not happy about it, but Jim and Andy find the guy to be fun. Jim and Andy take Frank to a strip joint, and he dies from the excitement.
When Jim & Andy go to Las Vegas on a business trip, Cheryl & Dana also go for a vacation. Cheryl secretly hopes to reunite Jim and his sister Roxanne. Roxanne typically uses people. When Jim and Roxanne make up, she says she needs money.
After Jim makes up with Roxanne, she asks for money. Since Jim is hesitant, Roxanne settles on Dana and they get married. Now that Roxanne has money, she starts seeing her old boyfriend again. Also, their meeting in Vegas turns out bad.