Jim and Cheryl are the perfect middle class American couple. Happily married, living in a suburban house with two adorable (but loud) little girls and a baby boy, they really can't complain much about life – except for those couple fights that neither one can ever let go, like the time Jim shut the car door on Cheryl. This time the problem is their daughter, whom Cheryl can't leave alone on her first week at kindergarten. Jim says it's because she's a woman and decides to take Ruby himself, but he also can't leave her behind. Things heat up when Cheryl discovers that not only has he been hiding it from her, but he also changed Ruby's school without talking to her. Meanwhile, Jim and Cheryl try to help Andy make up with his girlfriend.
Cheryl's 15 year-old cat Mr. Feeney dies and she wants Jim to bury it on the backyard, but Jim desperately wants to go to the Bears game. 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 current life. Jim, feeling guilty, provides a proper funeral for Mr. Feeney and gets her a brand new dog, which she doesn't like very much at first, but starts to accept it later.
On Jim and Cheryl's 10th Anniversary, Jim pays Dana to buy him an anniversary gift to give to Cheryl. However, Dana buys a beautiful and touching charm bracelet, going over the spending limit in the process, and Cheryl finds out that all her anniversary gifts over the past ten years were bought by Dana.
It's Thanksgiving and Jim and Andy are going bowling. Cheryl doesn't like the idea very much, so she sends the girls with him. Jim has a perfect game, but just when he was about to bowl his final strike, the power goes off and he is left with either waiting for it to return or giving up being perfect. Cheryl surprises him by bringing the Thanksgiving dinner to the alley so Jim's family and friends can witness his perfect game.
Andy has a new girlfriend, and Cheryl wants Jim to treat her nicely because not only is she Andy's first girlfriend sine Carrie, but also Ruby's piano teacher. During dinner, Alicia tells Jim she's a vegetarian, and not only that, but also a Peckers fan – a big insult to Jim. Alicia and Andy break up and get back together, but she keeps turning down invitations to have dinner at Jim and Cheryl's. The reason? She doesn't like being around Cheryl. Jim rubs it on her face until Cheryl confronts Alicia, who reveals it's only because she thinks Cheryl's too perfect.
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.
After Jim is diagnosed with high blood pressure, Cheryl decides to do everything to help him. She makes him special food, give him backrubs, and keeps asking about his day in order to free him from stress. But Jim doesn't know how to share so much and tells her an old financial problem of the firm. Cheryl stays up all night doing math to figure out a way out of the problem. Jim says she has a disease and is always trying to help people, which Cheryl responds with stop caring about him. In the end, they finally settle their issues when Jim says he loves her and would be a total mess without her.
It's Kyle and Andy's birthday, and Andy is feeling a little left out of his own special day. They decide to take him to a restaurant that serves a 4,5 lbs steak, and Jim offers to pay for the check because Cheryl isn't feeling equal to Dana, who's spending a lot of money on their kids. On the table, Dana says she doesn't mind paying the check because she makes more money than Jim, which enfuriates him. He buys a donkey for the girls so they can know he's the one they should go to if they want stuff (in this case, they wanted a poney, but "they'll never know the difference"), and it isn't until the donkey ruins a painting Dana bought for Kyle's room that they talk it out and settle their issues.
When the new DVD player breaks, Jim must find the receipt in order to exchange it. He can't find it anywhere and blames Cheryl of losing it. She says he was the one who lost it, and in order to "win" the fight, Jim buys another DVD player and tells Cheryl he exchanged the broken one. Later, Dana shows up with the receipt, in which Cheryl wrote her a recipe, and Cheryl - after realizing it was her fault after all - burns it. They get into a fight but soon decide to drop the point scoring and just be happy again.
Jim agrees to take the girls for the day while Cheryl and Dana go to a doctor's appointment. At the park, Jim leaves the girls with another mom and goes to the movies... where he's busted by Cheryl. Things go from bad to worse when he tries to retrieve the kids and can't remember who he left them with.
Jim buys a digital camera from one of Dana's ex-boyfriends, and it comes with stored pictures of the woman he dumped Dana for. Cheryl thinks it will make Dana feel better if she saw how ugly the new girl is, but Jim simply deletes the pictures because they weren't important enough for him. They start a fight about what's important to each one of them and Cheryl hides his new camera. Jim tries to get back at her, unsuccessfully. When Kyle starts to take his first steps, the camera is nowhere to be found and the moment is lost forever. That's when Cheryl realizes her actions didn't do any good. They make up and agree on paying more attention to what's important to each other.
Dana needs to buy a new car and Cheryl offers to go with her, but Jim says chicks are no good buying car 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. 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.
Cheryl wants to be friends with the new couple who just moved into the neighborhood. She has to be fast and do it before they talk to anyone else and get scared of them. After lending Janet the baby monitor, Cheryl schedules dinner with the new couple and has a hard time convincing Jim to go. When they get home back from the dinner, Cheryl is thrilled that it all went very well, and they're surprised when the baby monitor picks up Ted and Janet's conversation from their bedroom. The entire family gets addicted to eavesdropping on the couple, and Jim accidentally slips Ted's nickname for his penis. The new couple is outraged, and it takes Jim to make up a story about a homosexual experience he had in college to even the score and not lose their new friends.
Jim asks Cheryl not to intrude his space in the bathroom sink and in their closet, claiming she takes up too much space, and worse, HIS space. Cheryl tries to do something about by getting rid of some of her stuff, but Dana tells her it's time for women everywhere to show men they also have a need for space. Therefore, instead of doing what Jim asked her to, Cheryl buys even more clothes to jam up the closet. As a revenge, Jim decides to decorate their room in his own way. That starts a feud between them, until Jim falls down from the attic on their bed, breaking through the ceiling. He tells Cheryl that he needs his own space, and not because her stuff annoys him, but because he has the need to feel safe from the world sometimes. They settle their feud and agree on respecting each other's spaces.
Jim is taking the girls to their first Bears football game, and Cheryl asks him to be a good role model and try his best not to swear in front of them. At the game, Jim picks a fight with a Packers fan who was swearing in front of the girls, and the entire fight is televised, with Jim getting the nickname of "Packers Smacker". He finds glory with such nickname, but Cheryl doesn't like it at all. It only hits Jim the effects his actions might have on his children when Ruby hits Gracie in the nose. Jim has to have a talk with Ruby and hear Cheryl says that the next time he finds himself in a situation like on the football game, that he should just think what she would do and do it. But Jim finds redemption when Gracie refuses to eat sundae fudge because she thinks her butt's too big – something Cheryl was saying around the house not too long ago.
Dana gets selected to be on the reality show The Bachelor. At first she's sure her personality alone will be enough to entertain the guy, but Jim gives her advice on how to behave and what to say to the guy. Dana thinks he's full of crap, but after her date goes bad she tries Jim's recipe and scores a second date. She arranges with Cheryl to bring the bachelor over to their house for dinner, and Cheryl couldn't be more thrilled to be on national television with a remodeled house. Jim is also very proud that Dana only got so far thanks to him, but the situation quickly takes an unexpected turn when Jim accidentally overhears the bachelor saying Dana will be easy to bring to bed and then he'll dump her. Now he goes out of his way to save Dana and ends up scaring the guy away with stories about Dana being a psycho. Later he explains to her his behavior and says she'll meet someone who's good enough for her.
Cheryl drags Jim down to the church for the new reverend's mess, which is supposed to be "the next best thing". Jim sees some familiarity on him, and remembers he was the kid he played dodge-ball with back when they were kids. Jim also remembers that he threw the ball so hard at the guy he got a fat lip (and a funny nickname) for weeks (the nickname lasted for years). When Cheryl invites the reverend over for dinner, Jim freaks out, hoping he won't remember a thing. But Jim's hopes go down the drain when the reverend confronts him and later quits the church, giving his inability to forgive Jim as a reason. Feeling guilty, Jim apologizes and even takes on Gracie and Ruby's advice on offering Reverend Pierson a chance to throw a dodge-ball back at him.
Cheryl is thrilled when she is offered to be in charge of the set of the girls's Thanksgiving school play. She asks Jim to help her, and he's complaining they don't spend any time together because there's always someone around them. When they finally get alone on the set, they decide to be a little wild and do it behind the Plymouth rock. Unfortunately, Andy and the PTA president walk in on them. They promise to keep it quiet, but Jim and his big mouth brag about it with a divorced father who criticized married life. When Jim and Cheryl's sexual adventures are spread around the PTA board, Cheryl is fired from her set duties, and Jim, feeling guilty about it, stays up all night to finish the job for Cheryl.
Eddie, a country musician who's dating Dana, comes between Jim and his brother-in-law Andy. After hearing Jim and Andy's band practice, Eddie invites them to perform with him at the House of Blues. The catch: Eddie plays keyboards instead of Andy. An excited Jim accepts anyway and hopes to keep the gig a secret from Andy, who, of course, finds out. Encouraged by his sisters, the left-out architect decides to even the score by exploring new business horizons-without his contractor-partner Jim.
Jim's old friend Danny visits him, and brings his partner in crime, Laraine, with him. Cheryl and Dana offer to help Laraine pick out a dress for the police ball, and after realizing she has feelings for Danny, Cheryl convinces Jim to talk to Danny about asking her to the ball. Cheryl reveals to Jim that if it wasn't for Danny, they might never have gotten together, as they remember the time they met at a bar back in the 80's. But when Danny finally has the guts to talk to Laraine, he finds out that Andy already asked her out. Dana asks why can't she be Danny's date, since she made out with Cheryl's boyfriend the night she met Jim just so he would get out of the way. They all try to convince Andy to step aside what could be true love, but Andy reminds them of how he pretended to have a heart attack just so Jim would get rid of his girlfriend the night he met Cheryl. Finally, Andy agrees to help Danny and Laraine, as Jim and Cheryl conclude that despite all the help they got they still would have met.
Jim's old friend Danny visits him, and brings his partner in crime, Laraine, with him. Cheryl and Dana offer to help Laraine pick out a dress for the police ball, and after realizing she has feelings for Danny, Cheryl convinces Jim to talk to Danny about asking her to the ball. Cheryl reveals to Jim that if it wasn't for Danny, they might never have gotten together, as they remember the time they met at a bar back in the 80's. But when Danny finally has the guts to talk to Laraine, he finds out that Andy already asked her out. Dana asks why can't she be Danny's date, since she made out with Cheryl's boyfriend the night she met Jim just so he would get out of the way. They all try to convince Andy to step aside what could be true love, but Andy reminds them of how he pretended to have a heart attack just so Jim would get rid of his girlfriend the night he met Cheryl. Finally, Andy agrees to help Danny and Laraine, as Jim and Cheryl conclude that despite all the help they got they still would have met.
Cheryl is mugged at the mall parking lot, but instead of calling the police she chases the guy and tackles him to get her purse bag. When she tells Jim what happened, he decides to get two killer German shepherd to guard her. Cheryl doesn't like the idea, especially because the dogs are trained in German. One night, when the girls and Kyle are sleeping over at Dana's, Jim and Cheryl get locked into the bathroom after they mistakenly order the dogs to attack them and don't know how to order them to stop. The solution? Give the dogs drowsy medication. After that, Jim and Cheryl acknowledge that they could actually lose each other and start being warmer with one another.
Cheryl has to have dental surgery and asks Jim to stay besides her the whole time because she's scared of dentists. While Cheryl is sedated, Andy shows up saying he met blues legend Bo Diddley and Jim decides to meet him too, leaving Cheryl unattended. There's no harm since she's sedated, he justifies. But Cheryl finds out when Bo Diddley sends Jim a thank you basket with edible goodies and Jim confesses. They have a fight and the next day Cheryl goes out to the movies, leaving Jim in charge of the kids. Coincidentally, tickets for Bo Diddley's concert arrive at the house, but Jim wonders if that's some of Cheryl's tests. He goes but changes his mind and return to his kids at home.
Cheryl makes friends with another mom from the girls soccer team. The woman is sweet, yet a bit obnoxious. Jim is annoyed by her presence, but Cheryl insists on him being nice to her. Little by little, Cindy starts to get into their lives and tell them what to do and not to do. Jim ends up buying a hot tub from her husband, thinking that might drive them away, but instead it only pulls them closer. They show up unexpectedly on the tub, which is the final drop for Jim. He tells Cheryl it's time for her to come clean and confess to Cindy that they don't like her. Just when she finally does that, Cindy's husband offers Jim season tickets for the Bears. In order to undo the break up he asked Cheryl to do, Jim tells Cindy that Cheryl is under medication for mood swings and that he's willing to do them anything. They move in for a week, while Cheryl decides to take some time off at her sister's "for mental health".
A trained bird flies into Andy's head in the backyard and Gracie adopts it as her bird pet, Daphne. The bird is driving everyone insane and they all can't wait to get rid of it, but unfortunately Gracie developed a deep emotional attachment to it. When someone leaves the window opened and the bird flies out in the middle of the night, Jim and Andy team up to go look for it at the park the next morning. When they spot the bird, their first reaction is not to tell Gracie, but Jim doesn't want to lie to his daughter anymore. Later, the real owner show up at the house and Gracie is forced to say goodbye to her feathered friend. Or is the thought of running away to Mexico more appealing than that?
Jim and Andy are going to Vegas on a business trip and ask Dana to join them, since they need an extra help and she happens to be their "rabbit's foot" on gambling. Cheryl decides to join them and blackmails Jim when he says no at first. Cheryl has been secretly in touch with Jim's estranged sister Roxanne and plans for them to meet in Vegas. When they get there, Jim is not pleased to see his sister and tells Cheryl that no matter what she said he's sure she hasn't changed at all. Roxanne says she needs 2.000 dollars to start her business, which Jim takes as the first step on her plan, but Roxanne won't take either his or Cheryl's money. Instead, she gets it from her new husband: Andy, who has fallen head over heels for her and married her while the rest of the family was watching a show.
Andy is upset because no one approves or believes in his marriage to Roxanne. Jim goes to talk to her and walks in on her packing to run off with her ex boyfriend. He tries to stop her, unsuccessfully. Jim and Cheryl try to break the news to Andy before the business presentation, but he's so upset that he breaks down in tears on stage. While consoling Andy, Jim forgets about the foam hose and foam just floods the stage. Jim and Cheryl stroll in Las Vegas, glad that Andy is finally recovering from Roxanne and glad that their trip is over.
When Jim finds out that Cheryl has been paying 7 dollars to have the groceries delivered to their house, he insists that he does the shopping himself in order to save that incredible amount of money. Once at the supermarket, he sees how married men are "domesticated" by their wives and decides to rebel against Cheryl by shopping everything but the items on the list. Cheryl decides to turn the table on Jim and he does the same, until they end up going to a formal party on robes and underwear with their bodies all painted with lipstick. Cheryl finally gives in and they settle on paying the delivery boy the seven dollars in order to spare the Spice Channel subscription.
Jim is horrified when he sees his son Kyle with a green Packers ball. He tries by all means to change it for a Bears one, but the kid just can't let go of the green ball. Jim has nightmares about it and takes Kyle to his work in another attempt to get rid of the Packers ball. When he realizes there's nothing he can do about it, he does a little alteration on the ball so they can go to the Bears game peacefully.
Cheryl says a friend of hers got jewelry for his wife for no reason and Jim says he's probably cheating on her. After Cheryl takes it offensively that Jim won't buy her jewelry because he doesn't think he has to – after all, they are married and he isn't cheating – he goes out to shop for earrings, only to find out he knows nothing about Cheryl. After spending three days dedicating himself entirely to paying attention to Cheryl – with a bit of Andy's help – Jim finds out that Cheryl's friend was indeed cheating and they finally make up.
Jim and Cheryl encourage the girls to make a lemonade stand and raise money for their scooters. What was supposed to be a lesson about the value of the dollar turns into a racy competition among neighbors when Bill and his next door neighbor Driscoll set up little amusement parks in their years. Dana and Andy pitch in, while Cheryl tries to stay out of it – until she gets into a catfight with the neighbor's wife. Once the police is called in, Jim realizes he's lost the purpose of the lemonade stand and decides to give the girls the rest of the money for the scooters.
It's Halloween and Cheryl is trying to host "the" party so she can own Halloween in the neighborhood. Dana brings in her newest date, Hank, who carries an awful lot of similarities to Jim. While refusing to admit she's dating Jim, Dana realizes the truth when she accidentally pinches Jim's butt thinking it was Hank. The next day she and Cheryl have a fight over the whole situation, which leaves it up to Jim and Andy to fix the friendship between the two sisters.
Cheryl starts to feel taken for granted as she prepares Thanksgiving dinner. She suffers the ultimate insult when she gets stuck on the roof after retrieving her tablecloth that Jim had fashioned into a ghost for Halloween, and no one notices her absence until she unhooks the satellite. To apologize, Jim tells her that he, Dana and Andy will prepare the dinner. Jim never thinks that Cheryl, being the control freak that she is, would allow that to happen, so he doesn't make dinner. Unfortunately, neither does Cheryl.
Cheryl forbids Jim from throwing his cop friend Danny a bachelor party with beer and strippers. She fears that Danny will show up at his own wedding with a hangover – as Jim did at their wedding. Jim and his buddies decide to take Danny for a swim in bitter-cold Lake Michigan – forcing a hospital visit for Danny. The wedding morning, Danny stays in bed, moaning and groaning, and Cheryl frets, but the doctor assures everyone there's nothing wrong with him. Jim realizes Danny just has cold feet, so he tries to convince him to go through with his wedding to Laraine, a fellow cop.
Cheryl tries to impress her boastful cousin Mindy by posing as the lead singer of Jim's band – even though she has a terrible voice. Jim agrees to perform at Mindy's engagement party with Cheryl playing the part in order to teach his wife a lesson about embellishment by making a fool of herself. However, when Mindy tells Jim that her fiancé, Eric, is a record producer, he must decide between telling Cheryl the truth and making a bad impression on Eric.
Thinking it might get Cheryl to let him go on a fishing trip with Andy, Jim makes a "deposit" in the "marriage bank" by agreeing to go to a couples seminar with her. Jim's plans are foiled, however, when Dr. Ted, the marriage guru, declares the whole marriage bank mentality unhealthy and Cheryl learns Jim's real motives – so that Dr. Ted must intervene.
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.
Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gifts. But then Jim learns that a special blues tape Cheryl supposedly made for him when they were dating, and that made him fall in love with her, was actually made for her by an old boyfriend
Jim worries that Cheryl's romantic expectations will increase when his new brother-in-law, Ryan, showers Dana with flowers and gifts. But then Jim learns that a special blues tape Cheryl supposedly made for him when they were dating, and that made him fall in love with her, was actually made for her by an old boyfriend.
Cheryl, upset that Jim thinks her daily anecdotes are boring, steals Dana's story about meeting Oprah. Jim, now determined to out-do Cheryl, makes up a story about his construction office catching fire. But when Cheryl take the kids to see the damage, Jim and Andy, who are scrambling to make it look authentic, end up setting a real fire.
While Ryan is away, Dana and baby Tanner are staying at Jim and Cheryl's, until Jim starts complaining about the presence of the baby, so Cheryl wants him to stay at Andy's for a while. While Jim and Andy enjoy their male bonding, Cheryl and Dana are enjoying their time together too. At least, until Ryan returns.
Crazed about the fact that Cheryl joined a dinner party club, Jim insults the very creator of women, God, who then gives Jim the power to try to do a better job, but Jim ends up making women behave like Jim would. Also, when Andy tries to make guys more like women, he turns himself and Jim into oversensitive girly guys.
When Cheryl takes a greater interest in general safety and health, Jim feels stifled by her new rules and regulations. Just after Cheryl forces Jim to wear an I.D. badge during his morning jog, Jim is head-butted by a bull on a side road. While Cheryl learns that one can't anticipate every danger out there, Jim realizes that he's willing to do whatever it takes to make his family feel secure.
Cheryl and Jim have an evening at home without the kids and decide to stay in and just have dessert for dinner. But Jim's choice of pastries causes a spat which morphs into an all-out food fight. The next day they laugh off the night's argument; Jim is thrilled that they don't seem to have to talk things out. But then Andy, who's out for revenge on Jim for coaxing his kids to play pranks on him, counsels Cheryl to really dissect and analyze her marital arguments.
Without consulting with Cheryl, Jim transforms the garage into a cigar lounge and donates the kids' old clothes and furniture to charity. When Cheryl informs Jim that she is pregnant with twins, he is forced to retrieve all the stuff that he gave away, and has to deal with the fact that he is going to be a father of five.
Realizing that Andy didn't use the gift certificate that Jim gave him for his birthday, Jim decides to use the certificate to treat himself with a nice meal, but soon Jim finds himself in an uncomfortable situation when Andy remembers the certificate and decides to invite Jim to join him for a meal.
Dana puts Andy under hypnosis to learn why all of his relationships don't last longer than six weeks. Upon learning that it's due to Andy's low self-esteem, Dana decides to boost up Andy's confidence, but she ends up making things worse when Andy starts flirting with other women while on a date with Emily.
When Cheryl learns of Jim's plan to use their twins in a movie starring Steve Guttenberg to get some money for Christmas gifts, she refuses to let him do it, but Andy and Jim decide to go through with the plan anyway, only to have it backfire when the producers cut the kids hair to make them look alike.
Andy, desperate to impress Mandy with the perfect birthday gift, turns to Jim for advice. Jim counsels against givivng fancy jewelry, urging Andy instead to give a sentimental gift to win her over. But Andy's recollection of what has meaning to Mandy is way off base, and instead of being pleased with the gift, she thinks he's cheating on her.
Cheryl and her friends, eager to get an afternoon away from the kids, arrange a "Daddy and Me" group for Jim and other dads with young kids at their home. Jim makes the best of a potentially boring situation by turning babysitting into a sporting event--staging baby races where the dads bet on their kids and drink beer.
Cheryl forces Jim to donate time to charity. His reluctance turns to elation when he's rewarded with a thousand-dollar check for his efforts. Cheryl insists he return the check, but Jim is itching to buy himself somthing frivolous with the money. And to really test Cheryl's integrity, he spends the money on a pricey designer handbag for her.
When Jim chokes on a shrimp puff, he dies and arrives at Heaven's gate. With Jim on trial to prove his selfless acts on earth, best friend Andy is summoned to heaven to defend him. As Jim attempts to prove his good works to God, his sister-in-law, Dana, represents the Devil, arguing that Jim's selfishness should mean a certain trip to hell.