Jim happens to get free front row tickets to the Cubs game and wants to take Kyle to his first game. Unfortunately, Cheryl insists Kyle attend his first day at kindergarten instead. Jim decides to con Cheryl.
Ryan shocks everyone by offering to help with the dishes. Jim gives him a talking to and forbids him from giving Dana an expensive anniversary locket because it will make Jim look bad. Ryan gives it anyway. This means war: Jim against Ryan.
Cheryl is helping the homeless. Andy notices a letter from Playboy to Cheryl, she's been nominated in an essay contest. The winner gets to go to the Mansion. Jim decides to submit his essay as Cheryl's. But he forgets the media coverage.
Kyle is no good in basketball, but Jim says men don't quit, they try harder. So Cheryl challenges him to join Dana in a 10 km run. When Jim finds out he isn't fit enough do it, Andy tells him he has a foolproof plan.
Though Jim finds Cheryl's anecdotes boring, he advises Ryan that a husband must pretend to like a wife's stories because listening is foreplay. Cheryl hears it and argues with Jim. Jim boasts that he's an unbeatable showman. This means war!
Jim says he can help Andy get better dates by being his "chick whisperer". With a hidden microphone and an earpiece that connect Andy to Jim, Andy manages to get the hottest woman he's ever dated. Surely there must be a catch?
Something is bothering Jim, but he denies it. Following Dana's suggestion, Cheryl decides to con him into therapy, but fails. Enraged, Jim tells what's annoying him, and they find out it's only a part of a bigger problem.
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.
Jim's old college girlfriend Melissa invites him to lunch. Cheryl gives her blessing, insisting that it's an innocent meeting. Jim disagrees, but goes. Melissa says she wants to do business with Jim. At least at first.
The siblings' mom is coming for a Christmastime visit. Andy suspects that Ryan will try to dethrone Jim as the favorite son-in-law. Jim doesn't believe. But then the evidence starts to speak for Andy's theory.
Ruby's school is going to show her a sex ed video. The parents get a preview screening. The mere thought of his little girl learning about sex gets Jim upset, but not as upset as after he's seen the video.
Gracie and Ruby want to get their ears pierced but Cheryl believes that this will lead to the girls growing up too quickly and convinces Jim. Jim and Cheryl renew their wedding vows and Jim walks down the aisle with an earring.
Jim's birthday. As always, he gets presents he is not excited about, but now he finally reveals it to Cheryl. Cheryl just wants Jim to fulfill his potential. The next day Kyle gives Jim a stick - and he likes it. It has potential.
Jim ruins a trip to movies by stopping at a place where he claimed they met Eric Estrada a decade ago, but according to Cheryl it was someone else and they've been arguing about it ever since. Then an opportunity to solve it arises.
Dana and Cheryl shop at a sex toy party hosted by Bernice. Meanwhile, Jim brags how their sex life is as good as 15 years earlier. The next day, Andy and Ryan are all giggly, and Jim becomes anxious to see what Cheryl bought.
After Jim makes one of his neighbors cry, Cheryl convinces him to be more sensitive. But "Polite Jim" later finds out that the neighbor was crying over something else, and not Jim's outburst. Worst of all, she apologized with a pie--which Cheryl kept from him!
The guys are preparing for the annual St. Patrick's day green man ritual. Cheryl becomes worried as this could affect the churchs board decision to allow Cheryl to join the committee. But Cheryl gets into more trouble than Jim.
Dana announces her pregnancy. Ryan is excited, but Jim gives him a speech about the downsides of living with a pregnant woman. He offers to guide Ryan through Dana's pregnancy. But Jim's relationship with the pregnancy doesn't stop there.