According to Jim: Season 5

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, much to Jim's dismay.

Out-of-shape Jim enters a 10K marathon to teach Kyle, who wants to quit basketball, a lesson about not being a quitter, but he cheats to get to the finish line first.

Cheryl, upset that Jim thinks her daily anecdotes are boring, steals Dana's story about meeting Oprah Winfrey. 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 and cause an explosion.

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 is being pestered by Dana to get on with renovations that seem to be taking for-ever. After he pops over to get on with it, Ryan leaves him with Dana sleeping up-stairs, where Jim over-hears her dreaming, about Jim.

Cheryl encourages Jim to meet a former girlfriend, Melissa Evans, who 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 a sex education video that is shown at Ruby's school, Jim realizes that he was in the video when he was young, at the age thinking it was for a horror movie.

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. But Cheryl gets annoyed and lets them pierce their ears and when Jim finds out he makes his own earring and wears it on the day he and Cheryl are renewing their vows.

It's Jim's birthday and he gets upset when Cheryl gives him gifts he does not want, but is really happy when Kyle gives 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. Out of curiosity, Cheryl buys one, but won't tell Jim. To make it worse, Jim finds the toy.

Jim gets mad when he finds out that his neighbor, Julie (guest-star Julie Newmar), has been writing children books and basing them on him.

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

Jim believes that Bill (guest-star Joseph Bologna), the father of one of Ruby and Gracie's 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 starts 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.