Jim finds something in common with the Devlins: fandom of The Bulls. He starts believing that the Devlins are a good luck charm. When Cheryl forces him to watch a game without the Devlins, he starts meeting them secretly on game nights.
While having dinner with Cheryl, Dana & Ryan, Jim gets jealous over a male waitress. He reveals to Ryan that he's just pretending, to please Cheryl. Ryan sees it working and wants to learn. So Jim teaches, but forgets one lesson.
Cheryl rents a chick flick and claims that Jim should watch it because women like sensitive men. Jim denies this, but when Andy watches the movie, Jim is drawn in. Then Cheryl returns before the movie ends. Jim has to finish it secretly.
Cheryl finds out that Jim made Kyle lie about his age at the cinema, and lectures how there is only right and wrong. Then Dana enlists her to cook for Ryan who thinks Dana is doing the cooking. When Jim finds out, it's only the start.
Dana's driving Ryan nuts with the wedding preparations. Jim assures him "there's always a way out." Ryan puts the advice to use. When Cheryl suggests Dana use her 1991 dress, Jim panics. As it happens, it burned in 1991. What way out now?
Following attractive delivery girl Alicia's suggestion, Jim grows a mustache. Cheryl hates it and tries to make him lose it by dying her hair dark - but Jim loves it! Then Cheryl meets Alicia and starts manipulating Jim through her.
Dana and Ryan's wedding is approaching and Dana needs someone to represent her late father in the traditional father & bride dance. Andy is a disaster and Jim is known to have no dancing skills. How can he make Dana feel better?
Jim's neighbor Bertram gives Cheryl 2 opera tickets, but Jim won't go with her. So she asks Bertram. When Cheryl wants to go to see a foreign film, Jim asks Bertram to accompany her. Then the guys remind him that Bertram is *still* a man.
April Fool's Day. Jim has retired from pranks. Cheryl brings his baseball cards to the garage where his band rehearses. Then Jim's most valuable card vanishes. After that, Andy tells that Beltzman, the guitarist, died. Is it a coincidence?
Jim & Cheryl find a way to get free time by moving the clock and sending the kids to bed early. Then comes the day they are to try making a baby, but now neither of them wants a baby and doesn't want to hurt the other by admitting it.
Jim & Andy take part in a hot dog eating contest. Jim tells Cheryl that since women lack competitiveness, a man will always win. But then an Asian woman, Yoki, is declared winner, and Cheryl revels in it. Worse, Andy starts dating Yoki.
Cheryl throws a bachelorette party for Dana, but it's a bit underwhelming. Jim secretly taped it and, frustrated, offers to throw Dana a real bachelorette party. Against her better judgment, Dana accepts.
Ryan wants to go stock car racing and Dana threatens to cancel the wedding if he endangers himself. Cheryl has to teach Dana the basics of a Man and His Thing. Meanwhile, Jim teaches Ryan about the Sovereignty of a Man.
Cheryl has a nightmare about Dana's wedding. When the priest needs to picked from the airport, Cheryl forbids Jim from participating. Upset that Cheryl doesn't trust him, Jim tags along with Andy who's picking up the priest.
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.