Cheryl can't leave Ruby alone on her first week at kindergarten. Jim says it's because she's a woman and decides to take her himself, but he also can't leave her behind. Jim not only can't leave Ruby alone he ends up changing schools for her which causes fighting between him and Cheryl.
Jim and Cheryl find their romantic getaway to the Bahamas set to work out perfectly, with Dana babysitting the kids. However, at the last minute, Dana is not able to babysit. In the meantime, Andy becomes a little too obsessed with making the perfect tree house for Grace and Ruby.
Cheryl's 15 year-old cat Mr. Feeney dies and she wants Jim to bury it on the backyard, but Jim wants to go to the Bears game with Dana and Andy. He sticks the cat in the garage freezer, planning on burying it after the game, but Cheryl finds out before he comes home. She is hurt that Jim doesn't listen to her nor care about a cat that has been longer with her than anything in her life. Jim makes it up to her by getting the family a dog and giving her cat a proper burial in the backyard.
On Jim and Cheryl's 10th Anniversary, Jim pays Dana to buy him an anniversary gift to give to Cheryl. Dana buys a beautiful and touching charm bracelet and Cheryl finds out that Dana bought the bracelet when Jim can't tell her the meaning of the charms that are on the bracelet. She also finds out that all her anniversary gifts over the past ten years were bought by Dana.
On Halloween, Cheryl has forbidden Gracie to go trick-or-treating. However, not wanting his daughter to miss out on the fun of the halloween spirit, Jim sneaks her out anyway. Andy becomes convinced that he's being stalked by an ex-girlfriend.
Jim and Cheryl find themselves wondering if they've set too many rules for their household when they find themselves arguing over whether to put a TV in the girls' room, making Jim promise Cheryl not to ride his motorcycle, and Ruby then tells Jim that Cheryl has been smoking again.
Cheryl is left alone to cook Thanksgiving dinner while Jim and Andy go bowling for a charity event. Worse, Jim invited friends to Thanksgiving dinner without telling Cheryl and while Jim is still bowling.
Andy starts dating Ruby's piano teacher. When the two couples get together for dinner, Jim finds out the piano teacher is a vegetarian, a feminist, and a Packards fan. These are three hot buttons for Jim.
Cheryl's mother is coming to visit them for Christmas and wants to stay at their house. Jim and Cheryl, however, prefer that she stayed at a hotel but don't know how to bring it up without insulting Maggie. After Jim tells Maggie that Cheryl wants her in a hotel, Maggie gives her grandma's pearl necklace to Dana. Cheryl's upset and goes to the airport to ask her mother' forgiveness, where she learns Dana only got the necklace because she doesn't have anyone in her life like Cheryl has Jim. Meanwhile, the girls think Andy is Santa.
Cheryl leaves Jim in charge of their kids and some other kids who were there to play with the girls during a Bears game. The next day, one of the kids mom calls Cheryl saying her daughter dame home repeating a swearing she heard from Jim. Cheryl apologizes for him and Jim is insulted that she always automatically takes the other person's side. Cheryl apologizes, and not too later Grace repeats the exact same word. Jim decides to teach her not to repeat it by making her say it non stop until she can't say it again. It works. 5 days later, at Ruby's ballet presentation, she slips, falls and says the word, unmasking Jim's guilt.
Cheryl returns home from the gym, and tells Jim she had a great time playing racquetball. She asks Jim to play racquetball with her but he declines. She tells him he is just afraid he will lose, and then the game becomes a challenge.
Andy helps Dana with taxes. Dana watches Jim & Cheryl's children while they go on a date. Jim finds a parking place, but before he can park, someone else takes it. Jim is angry and keeps talking about the spot while they eat dinner.
Andy & Kyle share the same birthday. Dana gives Kyle a large custom painted mural for his bedroom, and plans to pay for everyone's dinner out. She comments she makes more money than Jim. Now Jim has to prove he can buy everything too.
Jim wants to exchange a broken DVD player within the warranty period but cannot find the receipt. He blames Cheryl for losing it, but she says it is not her responsibility to keep track of all his items.
Jim runs into Danny, a friend he has not seen in years. Danny is still single and accuses Jim of being a settled married man. Jim sets out to prove Danny wrong by both of them partying at bars all night like they used to do.
Cheryl has a day of errands and time with her friends. Jim has to watch the children, but when he has a chance to have the kids go to a friend's home, he readily drops the kids off. When Cheryl returns, he forgets where the kids are at.
Dana needs to buy a new car and Cheryl offers to go with her, but Jim says chicks are no good buying cars by themselves, because they'll get distracted with other less important things like mirrors or cup holders. Offended, Cheryl is determined to prove Jim wrong and actually gets Dana a car for a fair deal, but the car soon breaks down. Jim takes over the situation and goes down the dealership to manly handle the situation and deal with the salesman. The only thing he wasn't counting on was a very seductive female manager, who convinces Jim to trade in his minivan for a brand new sports car. Cheryl and Dana try to undo the deal, but they have no luck either. Jim and Andy return determined to overcome Gretchen's looks, but Mike Ditka's presence ruins it for them.
Jim and Cheryl have a new house guest when the pizza delivery boy moves in with them. Ronnie wants to do stand up comedy, but his father tells him he will never make money that way. Ronnie decides to move out of his father's house.
Jim takes the girls to their first baseball game, and Cheryl tells him to be on his best behavior and set a good example. At the game, Jim gets into a shouting match with another fan, and their argument ends up on the show broadcast.
Dana gets accepted to be on the reality show The Bachelor. Jim gives her advice on how to keep a man interested. When Dana and the bachelor visits Jim and Cheryl for dinner, the bachelor reveals to Jim he only wants to get Dana in bed.
Cheryl and Jim are organizing the school's Thanksgiving Day play, and when they are alone on the set, they decide to get intimate. Andy and the PTA President walk in on them, and the story gets spread. Cheryl is dismissed from the play.
Cheryl has to do everything to prepare for Ruby's birthday party since Jim seems to mess things up. On the day of the party, Jim ends up having to deal with all the little girls for the sleep over party.
Cheryl needs a root canal, but she does not want to have it done. Jim says he will go with Cheryl so she will have support. However, at the dentist office, Jim realizes that Bo Diddley is in the building and he wants to leave Cheryl.
Cherly's new friend is another soccer mom who Jim finds annoying. Cheryl enjoys her company, so the two families become social friends. Eventually, Jim tells Cheryl she has to break off the friendship.
Dana takes Ruby to the park, and a single father strikes up a conversation with her. When Dana realizes he thinks she is the mother of Ruby, she decides to keep up the charade. Cheryl asks Jim to exercise more.
Cheryl's mother comes to visit, and tells everyone she is engaged. Cheryl and Dana are not happy about it, but Jim and Andy find the guy to be fun. Jim and Andy take Frank to a strip joint, and he dies from the excitement.
When Jim & Andy go to Las Vegas on a business trip, Cheryl & Dana also go for a vacation. Cheryl secretly hopes to reunite Jim and his sister Roxanne. Roxanne typically uses people. When Jim and Roxanne make up, she says she needs money.
After Jim makes up with Roxanne, she asks for money. Since Jim is hesitant, Roxanne settles on Dana and they get married. Now that Roxanne has money, she starts seeing her old boyfriend again. Also, their meeting in Vegas turns out bad.
Jim is outraged to learn they pay for groceries to be delivered. Cheryl says they have deliveries for a lot of things. He says he will take over the job of grocery shopping and other errands himself to save money, but it does not work out.
Jim gets Cheryl a pair of expensive pair of earrings that is similar to the pair of earrings she usually wears. Cheryl accuses Jim of not knowing her. To get back in her good graces, Jim tries to notice everything and buys more gifts.
Jim tells Cheryl she is making a big deal of Ruby doing homework. Cheryl tells him that he should try it. Since Jim does not want to, he talks to Ruby's teacher to give less homework because Cheryl cannot read. His story gets back to Cheryl.
Dana's new date is similar to Jim in many ways. Cheryl teaches Dana that she is basically dating Jim, and when Dana realizes it is right, she gets upset at Cheryl for pointing out the similarities. Cheryl hosts a Halloween party.
Cheryl climbs the roof to get the tablecloth Jim tied there for a Halloween. When she is stuck on the roof and no one notices she is missing, she realizes she is taken for granted. Jim says he will make Thanksgiving dinner but then doesn't.
Dana does not have money to buy Jim a Christmas gift, so Cheryl tells her to just take one Cheryl already purchased and say it is from her. Dana ends up putting her name on the most expensive gift and claims it as hers to give.
Dana is fed up because she attracts only shallow men. Jim is in trouble because his bowling team is missing one player. It just happens that Reverend Pierson is the solution to both problems. Unfortunately, there is a catch.
Danny and Laraine announce their intent to marry, and Danny asks Jim to be his best man. Cheryl tells Jim he better not get Danny drunk at a bachelor party. So instead, Jim takes him for a cold swim in Lake Michigan and gets him sick.
Jim is troubled because his replacement in the commercial, Ted, gets to be a bit too intimate with Cheryl in front of camera. So when a role opens, he grabs it. Mysteriously, Kitson turns gay when Andy is in the table.
Gracie has been acting up lately, and Jim says that Cheryl's gentle ways are not working for improvement. Jim comes up with a harsh punishment plan but takes it too far when he blames her for something she did not do.
Jim is working hard to please his new client, Veronica, which actually means that he's making Andy work hard. Because the boss can't be seen working hard publicly. But then Andy and Veronica have a talk.
The girls made a large paper mâché bear for the school for team spirit. Jim has to take the bear to school in his truck, but he lost his truck in an arm wrestling match and does not want to tell Cheryl.
It's a battle of the sexes when it comes time to redecorate the bathroom. Jim says Cheryl never takes his opinion into consideration for changes to the house, so Cheryl decides to listen to his ideas. He wants a talking toilet.
Cheryl saves every piece of art work and homework from the kids, so she tells Jim to rent a storage unit to store everything. Jim decides to trash all of it because he does not think it will ever be needed again.
Dr. Ted from TV is holding a "Making Good Marriages Great" seminar in Chicago and Cheryl wants to go and get his autograph. Jim surprises her by suggesting that she *sign them up*. But he has an ulterior motive.
Cheryl's ex from high school, Doug, starts dating Dana, who invites him to dinner at Cheryl and Jim's. While Jim bonds with Doug, Cheryl starts showing signs of something that has troubled her for 15 years.
Jim gets a hole-in-one and celebrates himself tired. But he's supposed to give his sperm sample that day and the aforementioned activities are forbidden. He gets Andy to give the sample instead. Well, it seemed a good idea at the time.
Jim is supposed to spend a romantic evening with his wife, but he is torn because he wants to see a certain sports event that very same night. Desperate, he decides to con Cheryl - deluded that he can get away with it.
Jim sells his old grill to Andy for $200, but Cheryl says that Andy should have it for free. Jim agrees. Then things take a twist when Jim just cannot give the grill away for free. An escalating tug-of-war between Jim and Andy begins.
Jim and Cheryl argue over men and women having different inbred skills. When Chery and the kids get trapped in the garage because the females do not remember the code, Kyle opens the door with the code. Cheryl does not want Jim to find out.
Jim gets upset when Ruby stops giving him a goodbye kiss outside school. Cheryl explains that Ruby is going through a phase, and Jim tries to respect that. But when Ruby starts rebelling against him, he has to try really, really hard.
Jim's doctor tells him the sperm count is still too low - to increase it, he should have orgasms only when trying to make a baby and avoid his loud outbursts. Difficult, when Dana and a difficult customer give him cause for outbursts.
Christmastime. A man bumps his car into Jim's car and upsets him. Cheryl talks Jim into settling the issue officially. When Jim sees the man as Santa at the shopping mall, he gets into a dust-up with him. And things snowball from there.
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.
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.
At the television station, Jim is mistaken for a book author and ends up on the show. Jim gives his views of women trying to make men more like them, by forcing them to go to baby showers and the such. Cheryl is not happy about his views.
Jim convinces Dana that it will be all right for Ryan to attend to the birth of a baby of a well-known star in a war-torn country, then has to step up when she goes into labor and Ryan's still stuck there.
Things go wrong for Jim when he talks to God about having women be more like men. When Cheryl and Dana become just like Jim and Andy. Jim asks God to make men be more like women, but they turn into overly sensitive women.
Cheryl tells Jim to wear an ID badge when he goes running in the morning, but he does not want to. When he has an accident on his run, he is taken to the hospital without ID. Jim realizes he needs to take precautions for his family.
Cheryl goes to Florida to care for her mother when she is sick, leaving Jim alone to take care of the children. When neighborhood mom's find out Jim is struggling at home, they all pitch in to help. Each one thinks they are the only helper.
Jim still struggles with household duties while Cheryl is out of town, but has real problems when Ruby asks to go shopping for a training bra. Jim asks Dana to be the temporary mom for shopping. Turns out, Ruby is getting ready for a date.
Andy remembers the dinner gift card Jim gave him for his last birthday the day before it's due to expire and asks Jim to accompany him. The only problem is Jim felt slighted in giving it to Andy so he's already cashed it in.
Andy may have hit the jackpot with the new lady in his life, but Jim may have screwed it up while agreeing to chaperon the lady's two daughters who accompany his own to a teen aged girls' concert and loses them all.
When Mandy convinces Andy to not play tackle football with Jim and the guys, it's Jim who has to come up with a plan, after talking him into playing anyway, for covering up the fact that Andy DID play and got hurt in the process.
Cheryl and Jim are signed up for a volunteer event, but he does not want to participate. When he is accidentally giving money for his volunteer efforts, he plans to keep the money even though Cheryl tells him it is wrong to keep it.
Cheryl thinks Jim's home-made coupons for her birthday are just a disguise gift, so he has to buy her something else that will be the real gift. He buys Cheryl a used diamond necklace for her birthday.