Although Cheryl is against the idea, Kyle skips his first day of kindergarten to go to a Cubs game with Jim.
When Ryan begins to shower Dana with unexpected gifts, Jim worries he will be unable to meet Cheryl's romantic expectations. But then, he learns of a tape Cheryl made supposedly for him when they were first dating was made for her by an ex-boyfriend.
Jim learns more about the tape Cheryl supposedly made for him when they were first dating, but eventually learns that he will always come first in Cheryl's heart.
When Cheryl wins two tickets to visit the Playboy Mansion she chooses to take Dana rather than Jim.
Jim enters a 10k marathon to teach Kyle a lesson about quitting, but to complete the race he has to cheat.
When Jim lets Cheryl know that he finds her anecdotes boring, she steals Dana's story about meeting Oprah. Jim then tries to outdo her by telling a story of a fire where he works. But when Cheryl and the kids go to check out the damage, Jim and Andy end up accidentally setting a real fire when they try to fake the fire damage.
Jim is concerned when Kyle decides to dress as Cinderella for Halloween.
Jim assists Andy in meeting a gorgeous woman at a bar, but she turns out to be crazy.
Cheryl goes silent on Jim for three days in order to teach him about communicating.
Jim tries to turn Dana's erotic dreams about him around for a profit.
Cheryl reconsiders her suggestion that Jim go to a business lunch with an ex-girlfriend.
Jim and Cheryl compete with Ryan and Dana for the affections of Cheryl and Dana's visiting Mother, Maggie.
Jim and Cheryl discover that Jim was in a sex education video as a kid when they preview a tape to be viewed at Ruby's school.
After Cheryl stealthily takes the girls to have their ears pierced. Jim gets upset, leading the two to a second wedding ceremony.
Jim thinks Cheryl gives him birthday gifts that are supposed to change him.
Cheryl and Jim argue about Erik Estrada and something involving him 10 years ago.
Andy's new girlfriend invites Cheryl to a sex toy party.
A children's book character, written by Jim's neighbor, represents her view of him.
Jim tries to be more polite after he makes one of his neighbors cry.
The father of one of Jim's children's classmate may be Jim's dad that left when Jim was a kid.
Cheryl doesn't want Jim to get out of control on St. Patrick's Day.
Jim gets jealous of Ryan when Andy starts playing chess with him regularly.
Ryan happily announces that Dana is pregnant, but Jim warns him of the fluctuating hormones and mood swings that happen to women when expecting a baby. Then Jim has a dream where he is pregnant.