It's Halloween and Cheryl is trying to host "the" party so she can own Halloween in the neighborhood. Dana brings in her newest date, Hank, who carries an awful lot of similarities to Jim. While refusing to admit she's dating Jim, Dana realizes the truth when she accidentally pinches Jim's butt thinking it was Hank. The next day she and Cheryl have a fight over the whole situation, which leaves it up to Jim and Andy to fix the friendship between the two sisters.

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.

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

Cheryl, 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 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.

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.

When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection

When Cheryl takes a greater interest in general safety and health, Jim feels stifled by her new rules and regulations. Just after Cheryl forces Jim to wear an I.D. badge during his morning jog, Jim is head-butted by a bull on a side road. While Cheryl learns that one can't anticipate every danger out there, Jim realizes that he's willing to do whatever it takes to make his family feel secure.

When Ruby and Gracie can't seem to stop fighting, Jim is "forced" to read their diaries to determine the cause, only to realize that he needs to give out delicate motherly advice to them, while Cheryl is still away.