According to Jim: Season 5
| # | Air Date | Title |
| 1 | Sep 20 2005 |
Foul BallThe fifth season premieres with Jim sneaking off to a Cubs game with Kyle instead of taking him to his first day of kindergarten. |
| 2 | Sep 27 2005 |
The Tale of the Tape (1)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 b… |
| 3 | Sep 27 2005 |
The Tale of the Tape (2)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 b… |
| 4 | Oct 04 2005 |
Charity Begins at Hef'sWhen 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.… |
| 5 | Oct 11 2005 |
The RaceOut-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 first to the finish line. |
| 6 | Oct 18 2005 |
Anec-Dont'sCheryl, 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 co… |
| 7 | Nov 01 2005 |
The Chick WhispererJim 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. |
| 8 | Nov 08 2005 |
James & the Annoying PeachTo teach Jim the value of communication, Cheryl doesn’t speak to him for three days. |
| 9 | Nov 15 2005 |
The DreamJim tries to blackmail Dana when he finds out she’s having erotic dreams about him. |
| 10 | Nov 29 2005 |
Lean On MeCheryl 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… |
| 11 | Dec 13 2005 |
The Gift of MaggieWhen Cheryl and Dana’s mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection |
| 12 | Jan 10 2006 |
Sex Ed FredWhen Jim and Cheryl watch an sex education video that is shown at Ruby’s school, Jim realizes that he is watching a young him. |
| 13 | Jan 24 2006 |
Renewing VowsJim and Cheryl renew their wedding vows after Cheryl allowed the girls to get their ears pieced even though Jim had forbidden it. |
| 14 | Feb 07 2006 |
The StickIt’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. |
| 15 | Feb 07 2006 |
Mr. RightCheryl 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. |
| 16 | Feb 21 2006 |
Get Your Freak OnCheryl 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. |
| 17 | Feb 28 2006 |
The Grumpy GuyJim gets mad when he finds out that his neighbor Julie has been writing children books and basing them about him. |
| 18 | Mar 07 2006 |
Polite JimJim 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. |
| 19 | Mar 07 2006 |
Daddy DearestJim believes that Bill (played by Joseph Bologna), the father of one of Rubys and Gracies classmates is actually his real father that abandoned Jim when he was a child. |
| 20 | Mar 14 2006 |
The Thin Green LineCheryl 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. Patric… |
| 21 | Mar 21 2006 |
Jim's Best FriendWhen Andy stars playing chess with Ryan on a regular basis, Jim is convinced that he is losing his best friend. |
| 22 | May 02 2006 |
Belaboring the PointWhen 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. |