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 Kyle changes back into the dress. Jim, Andy, and Kyle all sit on the couch, Jim and Kyle persistent. Jim goes in the kitchen, sees an older Kyle who convinces Jim to let Kyle go as Cinderella. In the end, they all go as ladies and they trick-or-treat.
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 a a plot for himself next to a star football player.
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 a legendary 40- lb. psychotic bird christened "Angry Pete." Thanksgiving-themed episode.
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 huge account from a blowhard potential client (Tom Arnold).
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 them any gifts for Christmas.
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.
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 her new beau is paranoid and possessive.
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.
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 ago.
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 a chance meeting with the girl, Cheryl asks her to give Jim suggestions that will make him look ridiculous.
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 Andy decides to date the female champion.
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 wedding?
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.
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, on the Season Finale.
