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…

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

On Dana’s wedding day, Jim accidentally knocks the family’s favorite reverend unconscious with the car door, so he has to scramble to find a replacement preacher at the last minute,…

Jim actually remembers his and Cheryl’s anniversary – but Cheryl didn’t! Improvising, she gives him the photo album that covers years worth of memories. They start reminiscing.

Cheryl and Dana think they have cause to worry when Dana’s fianc – wants to race fast cars and Jim wants to take up skydiving.

When Cheryl’s prim and proper bachelorette party disappoints Dana, Jim and Andy treat Dana to a rowdy night she’ll never forget – but now will she make it to the…

Jim, certain he will win the annual hot dog eating contest, is humiliated when instead he loses to a petit woman (Suzy Nakamura), and his problems are further compounded when…

Jim and Cheryl adjust the clocks to get the kids to bed earlier so they can have more quality time together.

Jim is shocked to learn that his recently deceased friend will be buried with a rare baseball card he stole from Jim.

Jim’s pride in Gracie’s new-found spelling-bee aptitude quickly turns to dismay when he has to drive her to tournaments all over the state.

In order to avoid going to an opera with Cheryl, Jim asks an elderly widower to be her escort.

When Andy decides to learn how to dance for his sister’s wedding, he turns to Jim, a closet dancer, for help.

A hot delivery girl gives Jim some fashion advice, prompting him to grow a mustache, which Cheryl hates. Cheryl retaliates by becoming a brunette – but Jim loves it. After…

When Cheryl offers Dana the use of her wedding gown, Jim and Andy try to cover up the fact that the dress was destroyed in a fiery sports celebration years…

Cheryl cooks dinner for Dana and her boyfriend and lets him believe that Dana actually did the cooking.

Cheryl claims to like men who aren’t afraid to cry, but when Jim bursts into tears after a movie, she is surprised to find herself turned off by his sensitivity.

To make Cheryl feel desirable, Jim fakes a jealous rage in a restaurant and tries to teach Dana’s date to do the same, but the lesson backfires when Dana fears…

Jim buys a nanny-cam to spy on the sitter he didn’t want Cheryl to hire but learns something about Cheryl instead, prompting her to buy a camera of her own.

Jim befriends his obnoxious neighbors when he believes they bring good luck when he’s watching the Chicago Bulls.

Jim tangles with a department store Santa after the two are involved in a parking lot fender bender. Unfortunately, Jim’s kids witness the skirmish and are fearful Santa won’t leave…

Cheryl’s gynecologist (played by Mitch Rouse) forbids her from having sex with Jim until the time is right to get pregnant, and Jim eats crow in order to win a…

To prove his worth as a man, Jim — along with Andy — hunt a turkey for Thanksgiving, but on the hunt Jim is pursued — and shot — by…

Cheryl’s mother, Maggie, wants Jim, Cheryl and the family to rest someday in a family plot she reserved years ago, but Jim insists on his own family plot–then secretly reserves…

Ruby hurts Jim’s feelings when she invites Andy to a father-daughter dance instead of him.

Kyle wants to be Cinderella for Halloween. Jim is against it because he thinks he’s growing up to be a sissy. Jim buys Kyle a manly costume (a dinosaur) but…

Cheryl and Dana are forced to smash their way out of a locked garage, because they ignored Jim’s lesson on how to open the door from the inside.

Jim offers to give Andy an old barbecue grill, then decides Andy should pay for it.

Cheryl surprises Jim with a romantic evening, but it cuts into his planned TV boxing match.

Cheryl wants Jim to give up his vices so he can get her pregnant.

Jim chickens out of having a vasectomy, but Cheryl is so effusive in her praise that he’s unable to admit he didn’t go through with it.

Cheryl protests when a heat wave sends the family sneaking into a vacationing neighbor’s pool — until she starts sneaking over on her own.

Jim develops a friendship with Dana’s new boyfriend, despite the fact that the guy dumped Cheryl years ago.

Thinking it might get Cheryl to let him go on a fishing trip with Andy, Jim makes a “deposit” in the “marriage bank” by agreeing to go to a couples…

Pack rat Cheryl asks Jim to rent a storage unit to house seven years’ worth of the kids’ art projects, but Jim refuses to pay the fee, so he tosses…

Cheryl promises to take Jim’s opinions seriously when she decides to remodel the bathroom, until Jim insists it include a hideous high-tech stainless steel toilet – that talks.

Cheryl ask Jim to use his truck to transport a giant paper-mâché grizzly bear the girls made for “spirit week” to their school – except Jim just lost his truck…

Andy resents a wealthy client, but then decides to date her.

Jim’s sister, Roxanne, shows up on his doorstep, pregnant, and lets Andy believe he’s the father.

Gracie’s recent misbehavior makes Jim think she is lying about a friend giving her a new video game.

Jim takes umbrage at being replaced as the father in a promotional shoot for a cruise line.