Season 5 Episodes

Episode Guide

Belaboring the Point

Season 5, Episode 22 - Air Date: 5/2/2006
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.
Episode Guide

Jim's Best Friend

Season 5, Episode 21 - Air Date: 3/21/2006
When Andy starts playing chess with Ryan on a regular basis, Jim is convinced that he is losing his best friend.
Episode Guide

The Thin Green Line

Season 5, Episode 20 - Air Date: 3/14/2006
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.
Episode Guide

Daddy Dearest

Season 5, Episode 19 - Air Date: 3/7/2006
Jim believes that Bill (played by 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.
Episode Guide

Polite Jim

Season 5, Episode 18 - Air Date: 3/7/2006
Jim makes his own neighbor cry with complaining about his backyard barbecue, so he ends up taking polite lessons from Andy, in order to become a better person.
Episode Guide

The Grumpy Guy

Season 5, Episode 17 - Air Date: 2/28/2006
Jim gets mad when he finds out that his neighbor, Julie, has been writing children books and basing them about him.
Episode Guide

Get Your Freak On

Season 5, Episode 16 - Air Date: 2/21/2006
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.
Episode Guide

Mr. Right

Season 5, Episode 15 - Air Date: 2/7/2006
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.
Episode Guide

The Stick

Season 5, Episode 14 - Air Date: 2/7/2006
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.
Episode Guide

Renewing Vows

Season 5, Episode 13 - Air Date: 1/24/2006
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.
Episode Guide

Sex Ed Fred

Season 5, Episode 12 - Air Date: 1/10/2006
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.
Episode Guide

The Gift of Maggie

Season 5, Episode 11 - Air Date: 12/13/2005
When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection.
Episode Guide

Lean on Me

Season 5, Episode 10 - Air Date: 11/29/2005
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.
Episode Guide

The Dream

Season 5, Episode 9 - Air Date: 11/15/2005
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, uh-oh.
Episode Guide

James & the Annoying Peach

Season 5, Episode 8 - Air Date: 11/8/2005
To teach Jim the value of communication, Cheryl doesn't speak to him for three days.
Episode Guide

The Chick Whisperer

Season 5, Episode 7 - Air Date: 10/18/2005
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.
Episode Guide


Season 5, Episode 6 - Air Date: 10/18/2005
Cheryl, upset that Jim thinks her daily anecdotes are boring, steals Dana's story about meeting Oprah.
Episode Guide

The Race

Season 5, Episode 5 - Air Date: 10/11/2005
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 first to the finish line.
Episode Guide

Charity Begins at Hef's

Season 5, Episode 4 - Air Date: 10/4/2005
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.
Episode Guide

The Tale of the Tape: Part 2

Season 5, Episode 3 - Air Date: 9/27/2005
Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gifts.
Episode Guide

The Tale of the Tape: Part 1

Season 5, Episode 2 - Air Date: 9/27/2005
Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gifts.
Episode Guide

Foul Ball

Season 5, Episode 1 - Air Date: 9/20/2005
The fifth season premieres with Jim sneaking off to a Cubs game with Kyle instead of taking him to his first day of kindergarten.