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.
Jim is outraged to learn they pay for groceries to be delivered. Cheryl says they have deliveries for a lot of things. He says he will take over the job of grocery shopping and other errands himself to save money, but it does not work out.
Jim gets Cheryl a pair of expensive pair of earrings that is similar to the pair of earrings she usually wears. Cheryl accuses Jim of not knowing her. To get back in her good graces, Jim tries to notice everything and buys more gifts.
Jim tells Cheryl she is making a big deal of Ruby doing homework. Cheryl tells him that he should try it. Since Jim does not want to, he talks to Ruby's teacher to give less homework because Cheryl cannot read. His story gets back to Cheryl.
Dana's new date is similar to Jim in many ways. Cheryl teaches Dana that she is basically dating Jim, and when Dana realizes it is right, she gets upset at Cheryl for pointing out the similarities. Cheryl hosts a Halloween party.
Cheryl climbs the roof to get the tablecloth Jim tied there for a Halloween. When she is stuck on the roof and no one notices she is missing, she realizes she is taken for granted. Jim says he will make Thanksgiving dinner but then doesn't.
Dana does not have money to buy Jim a Christmas gift, so Cheryl tells her to just take one Cheryl already purchased and say it is from her. Dana ends up putting her name on the most expensive gift and claims it as hers to give.