The fifth season premieres with Jim sneaking off to a Cubs game with Kyle instead of taking him to his first day of kindergarten.

Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gifts. But then Jim learns that a special blues tape Cheryl supposedly made for him when they were dating, and that made him fall in love with her, was actually made for her by an old boyfriend

Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gifts. But then Jim learns that a special blues tape Cheryl supposedly made for him when they were dating, and that made him fall in love with her, was actually made for her by an old boyfriend.

When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion in a charity-raising contest that Jim secretly entered her in, she decides to take Dana instead of him.

Cheryl, upset that Jim thinks her daily anecdotes are boring, steals Dana's story about meeting Oprah. Jim, now determined to out-do Cheryl, makes up a story about his construction office catching fire. But when Cheryl take the kids to see the damage, Jim and Andy, who are scrambling to make it look authentic, end up setting a real fire.

Jim helps Andy pick up a beautiful woman in a bar, but she turns out to be crazy -- and eventually leaves Andy and stalks Jim instead.

To teach Jim the value of communication, Cheryl doesn't speak to him for three days.

Jim tries to blackmail Dana when he finds out she’s having erotic dreams about him.

Cheryl encourages Jim to meet a former girlfriend wants to discuss business for lunch, and then regrets it when she becomes convinced that the old flame has romantic intentions.

When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection

When Jim and Cheryl watch an sex education video that is shown at Ruby's school, Jim realizes that he is watching a young him.

Ruby and Gracie want to get their ears pierced but Cheryl believes that this will lead to the girls growing up too quickly and convinces Jim. Jim and Cheryl renew their wedding vows and Jim walks down the aisle with an earring.

It's Jim's birthday and he gets upset when Cheryl gives him gifts he does not want, but is really happy when Kyle give him a stick for his birthday.

Cheryl and Jim get into a disagreement about Erik Estrada, and Jim tries to prove that the incident that occurred ten years ago was not wrong.

Cheryl believes she's attending a tasteful lingerie party, but is shocked to learn the hostess is selling sex toys and Cheryl buys one, but won't tell Jim.

Jim gets mad when he finds out that his neighbor Julie has been writing children books and basing them about him.

Jim makes his own neighbour cry with complaining about his backyard barbeque, so he ends up taking polite lessons from Andy, in order to become a better person.

Jim believes that Bill, the father of one of Rubys and Gracies classmates is actually his real father that abandoned Jim when he was a child.

Cheryl gives her best to assure herself a spot on the Church Committee, and in order to get that, she forbids Jim to do his annual "Green Man" routine on St. Patrick's day. However, her plans are ruined when she gets arrested.

When Andy stars playing chess with Ryan on a regular basis, Jim is convinced that he is losing his best friend.

When a proud and happy Ryan announces that Dana is pregnant, Jim warns him of Dana's upcoming hormone swings, and ends up dreaming that he is pregnant.