September 20, 2005 • 22m
The fifth season premieres with Jim sneaking off to a Cubs game with Kyle instead of taking him to his first day of kindergarten.
September 27, 2005 • 22m
Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gif...Read more
September 27, 2005 • 23m
Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gif...Read more
October 4, 2005 • 22m
When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion in a charity-raising contest that Jim secretly entered he...Read more
October 11, 2005 • 23m
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 c...Read more
October 18, 2005 • 23m
Cheryl, upset that Jim thinks her daily anecdotes are boring, steals Dana's story about meeting Oprah. Jim, now determined to out-...Read more
November 1, 2005 • 23m
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.
November 8, 2005 • 23m
To teach Jim the value of communication, Cheryl doesn't speak to him for three days.
November 15, 2005 • 23m
Jim tries to blackmail Dana when he finds out she’s having erotic dreams about him.
November 29, 2005 • 23m
Cheryl encourages Jim to meet a former girlfriend wants to discuss business for lunch, and then regrets it when she becomes convin...Read more
December 13, 2005 • 23m
When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection
January 10, 2006 • 23m
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.
January 24, 2006 • 23m
Ruby and Gracie want to get their ears pierced but Cheryl believes that this will lead to the girls growing up too quickly and con...Read more
February 7, 2006 • 22m
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.
February 7, 2006 • 23m
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.
February 21, 2006 • 22m
Cheryl believes she's attending a tasteful lingerie party, but is shocked to learn the hostess is selling sex toys and Cheryl buys...Read more
February 28, 2006 • 23m
Jim gets mad when he finds out that his neighbor Julie has been writing children books and basing them about him.
March 7, 2006 • 23m
Jim makes his own neighbour cry with complaining about his backyard barbeque, so he ends up taking polite lessons from Andy, in or...Read more
March 7, 2006 • 22m
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.
March 14, 2006 • 23m
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...Read more
March 21, 2006 • 22m
When Andy stars playing chess with Ryan on a regular basis, Jim is convinced that he is losing his best friend.
May 2, 2006 • 23m
When a proud and happy Ryan announces that Dana is pregnant, Jim warns him of Dana's upcoming hormone swings, and ends up dreaming...Read more