In this earthy family comedy, Jim is the macho Everyman who challenges his gorgeous and feisty wife, Cheryl, with his stubborn manliness but contagious charm. Tagging along with this duo of happily married opposites are their three precocious kids. A success at his construction business and the family breadwinner at home, Jim feeds his other passion - blues music - playing with his six-man garage band. He keeps Cheryl in turmoil with his boyish bravado and ever willful antics, but their underlying love guarantees that they are in this marriage for keeps.
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 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.
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.
Cheryl finds herself falling for a guy that Jim has setup for Dana.
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.
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.
Jim and Cheryl agree to let Ruby model for a print ad as a one-time thing, but when the photographer calls her a natural, Jim gets Ruby an agent.
Cheryl decides to go behind Jim's back and loan Andy $1,000 for a downpayment on a new condo but finds the money is missing.
Cheryl does something uncharacteristic for her - she gives Jim a sexy portrait of herself for Valentine's Day. When she finds out Jim shares the picture with all his friends, she is mortified.
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.
Jim gets hurt after jumping on a pogo stick and goes to the doctor. There, he finds out he has high blood pressure and has to start taking pills everyday. Cheryl tries to reduce the stress for Jim.
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 friend's home, he readily drops the kids off. When Cheryl returns, he forgets where the kids are at.
Jim has to deal with Cheryl's suspicions about a surprise birthday party for her, he then goes to a bowling with the Chicago Bears charity event on her birthday which upsets her more after she has ruined the planned surprise party for her.
Jim and Cheryl clash over a digital camera. He deletes a picture she wanted to keep, so she hides the camera from him.
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 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.
Kyle has a new favorite toy - a Packers Team football. Since Jim's favorite team is the Chicago Bears, he does not like that Kyle has a different team's ball.
Cheryl wants Jim to give up his vices so he can get her pregnant.
Cheryl surprises Jim with a romantic evening, but it cuts into his planned TV boxing match.
Jim offers to give Andy an old barbecue grill, then decides Andy should pay for it.
The fifth season premieres with Jim sneaking off to a Cubs game with Kyle instead of taking him to his first day of kindergarten.
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 realizes that Cheryl has been spoiling their son Kyle for way too long, so he decides to make him a man by teaching him how to throw a perfect punch in self defense. However, things get out of control when little Kyle gets suspended for repeatedly hitting the school bully.
Jim ends up on a talk show after claiming that men shouldn't let women feminize them, and then goes to Dana's co-ed baby shower to prove his point.
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.
Cheryl feels down when she can't use her sexuality to get a dinner table at a restaurant, so Jim tries to cheer her up by writing letter as a 'water delivery guy', but his plan soon makes Jim doubt if Cheryl is attracted to him or the delivery guy.
Jim guilts the older kids into doing household chores after Jonathan's special blanket goes missing.
When Dana, Cheryl's sister and best friend, moves away, Jim realizes he must find Cheryl a new friend as soon as possible.
Jim and his band win a chance to play for a child pop sensation Jami McFame, but when the star gives them an attitude, Jim decides to set her straight.
Complete episode guide for According to Jim with detailed information about every season and episode including air dates, summaries, ratings, and streaming availability in United States.
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Jim and Cheryl meet the new neighbors and find out that they can hear their conversation through the baby monitor. When the neighbors find out, Jim tries to come up with a story to smooth things over.
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 wants his own space in the house for his own things and for a place where he can be alone. Cheryl starts to thin out her closet, but Dana convinces her to get more items.
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.
The family goes to church, and Jim realizes he knows the new minister. When Jim was young, he and the reverend played dodge ball together.
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 is hoping to have the family invited to a neighbor's popular annual Christmas party, but Jim dashes her hope when he fights with the neighbor's husband.
Jim is excited when Dana's new boyfriend asks him to play backup music at a bar. The offer does not include the other members of Jim's band, and Jim tries to do it without Andy finding out.
When Jim reviews the credit card statement, he finds the bank made an error and now has surplus money. Jim takes Cheryl out to an expensive dinner with the money.
Jim and Cheryl's friend Danny visits. He brings his police officer partner with him. Cheryl realizes that Laraine likes Danny and hopes he will ask her to the policeman's ball.
Jim & Cheryl's friend Danny, and Andy, retell the story how they helped Jim and Cheryl get together.
Jim has another quick-rich scheme, and much to Cheryl's dismay, Jim, Andy and Dana think it is a good idea. Jim's idea is to make a doll who has gas movements.
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.
When an old girlfriend of Jim's comes to dinner, she accidentally reveals things to Cheryl that Jim wanted kept secret about them.
Cheryl becomes a Wonder Woman when she pursues a man who tries to steal her purse. Jim finds out about the attack on Cheryl and goes overboard in trying to protect the family by getting killer dogs.
Cheryl is upset when one of Jim's new clients makes a pass at her and Jim does nothing about it.
Jim talks to Dana's boss about his treatment of employees. Dana ends up getting fired.
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.
Cheryl finds the perfect gift for Jim's birthday on an online website and starts to bid on it. Another person is also bidding for the same perfect gift - Jim.
An exotic bird flies into Jim's back yard, and Gracie decides to keep it as a pet. The bird is loud and annoying, but Gracie refuses to let her parents get rid of it.
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 wins a water-bed when playing bingo at a church fund-raiser. The pastor realizes Jim cheated, and talks to him about doing the right thing.
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.
The girls get permission to open a lemonade stand to earn money. When the neighbors start a better lemonade stand in competition, Jim, Cheryl and the others up the competition.
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.
Jim takes the girls to see a scary movie even though Cheryl tells him not to. When the girls have nightmares at bedtime, Cheryl thinks she did something wrong.
Jim seems to always be busy helping a friend when he and Cheryl are to visit with some friends. Cheryl realizes this happens only when it is a specific couple.
Jim is tired of Cheryl always picking activities for them as a couple, especially the cooking class which was a disaster. He picks paint-ball for the next activity, thinking she will hate it.
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.
Jim is puzzled when Cheryl apologizes to him in the morning, but he accepts the apology and decides to use it against her to get out of everything he does not want to do.
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.
The house across the street from Jim & Cheryl is on sale. The Devlins visit and announce they are placing a bid on the house. Jim & Cheryl are upset and thinking of moving to get away from them.
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.
Cheryl decides to sing in Jim's band to prove to her cousin that she has talent. Trouble is, Cheryl cannot sing.
At Dana's new job, she gets to cast a family for a vacation commercial. She hires Cheryl and her family. The producer likes everyone except for Jim.
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's sister Roxanne visits Cheryl and Jim. She tells them she is going to have a baby, and Andy is the father.
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.
Cheryl promises to take Jim's opinions seriously when she decides to remodel the bathroom, until Jim insists it include a hideous high-tech stainless steel toilet – that talks.
Pack rat Cheryl asks Jim to rent a storage unit to house seven years' worth of the kids' art projects, but Jim refuses to pay the fee, so he tosses everything out, thinking Cheryl won't notice – until she needs some of the projects for a special retirement party for Ruby's art teacher.
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.
Jim develops a friendship with Dana's new boyfriend, despite the fact that the guy dumped Cheryl years ago.
Cheryl protests when a heat wave sends the family sneaking into a vacationing neighbor's pool -- until she starts sneaking over on her own.
Jim chickens out of having a vasectomy, but Cheryl is so effusive in her praise that he's unable to admit he didn't go through with it.
Cheryl and Dana are forced to smash their way out of a locked garage, because they ignored Jim's lesson on how to open the door from the inside.
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.
Ruby hurts Jim's feelings when she invites Andy to a father-daughter dance instead of him.
Cheryl's mother, Maggie, wants Jim, Cheryl and the family to rest someday in a family plot she reserved years ago, but Jim insists on his own family plot--then secretly reserves a a plot for himself next to a star football player.
To prove his worth as a man, Jim -- along with Andy -- hunt a turkey for Thanksgiving, but on the hunt Jim is pursued -- and shot -- by a legendary 40- lb. psychotic bird christened "Angry Pete."
Cheryl's gynecologist forbids her from having sex with Jim until the time is right to get pregnant, and Jim eats crow in order to win a huge account from a blowhard potential client.
Jim tangles with a department store Santa after the two are involved in a parking lot fender bender. Unfortunately, Jim's kids witness the skirmish and are fearful Santa won't leave them any gifts for Christmas.
Jim befriends his obnoxious neighbors when he believes they bring good luck when he's watching the Chicago Bulls.
Jim buys a nanny-cam to spy on the sitter he didn't want Cheryl to hire but learns something about Cheryl instead, prompting her to buy a camera of her own.
To make Cheryl feel desirable, Jim fakes a jealous rage in a restaurant and tries to teach Dana's date to do the same, but the lesson backfires when Dana fears her new beau is paranoid and possessive.
Cheryl claims to like men who aren't afraid to cry, but when Jim bursts into tears after a movie, she is surprised to find herself turned off by his sensitivity.
Cheryl cooks dinner for Dana and her boyfriend and lets him believe that Dana actually did the cooking.
When Cheryl offers Dana the use of her wedding gown, Jim and Andy try to cover up the fact that the dress was destroyed in a fiery sports celebration years ago.
A hot delivery girl gives Jim some fashion advice, prompting him to grow a mustache, which Cheryl hates. Cheryl retaliates by becoming a brunette - but Jim loves it. After a chance meeting with the girl, Cheryl asks her to give Jim suggestions that will make him look ridiculous.
When Andy decides to learn how to dance for his sister's wedding, he turns to Jim, a closet dancer, for help.
In order to avoid going to an opera with Cheryl, Jim asks an elderly widower to be her escort.
Jim's pride in Gracie's new-found spelling-bee aptitude quickly turns to dismay when he has to drive her to tournaments all over the state.
Jim is shocked to learn that his recently deceased friend will be buried with a rare baseball card he stole from Jim.
Jim and Cheryl adjust the clocks to get the kids to bed earlier so they can have more quality time together.
Jim, certain he will win the annual hot dog eating contest, is humiliated when instead he loses to a petit woman, and his problems are further compounded when Andy decides to date the female champion.
When Cheryl's prim and proper bachelorette party disappoints Dana, Jim and Andy treat Dana to a rowdy night she'll never forget - but now will she make it to the wedding?
Cheryl and Dana think they have cause to worry when Dana's fiance - wants to race fast cars and Jim wants to take up skydiving.
Jim actually remembers his and Cheryl's anniversary - but Cheryl didn't! Improvising, she gives him the photo album that covers years worth of memories. They start reminiscing.
On Dana's wedding day, Jim accidentally knocks the family's favorite reverend unconscious with the car door, so he has to scramble to find a replacement preacher at the last minute.
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.
When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion in a charity-raising contest that Jim secretly entered her in, she decides to take Dana instead of him.
Out-of-shape Jim enters a 10K marathon to teach Kyle, who wants to quit basketball, a lesson about not being a quitter -- but he cheats to get first to the finish line.
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.
Jim helps Andy pick up a beautiful woman in a bar, but she turns out to be crazy -- and eventually leaves Andy and stalks Jim instead.
To teach Jim the value of communication, Cheryl doesn't speak to him for three days.
Jim tries to blackmail Dana when he finds out she's having erotic dreams about him.
Cheryl encourages Jim to meet a former girlfriend wants to discuss business for lunch, and then regrets it when she becomes convinced that the old flame has romantic intentions.
When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection
When Jim and Cheryl watch an sex education video that is shown at Ruby's school, Jim realizes that he is watching a young him.
Ruby and Gracie 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.
It's Jim's birthday and he gets upset when Cheryl gives him gifts he does not want, but is really happy when Kyle give him a stick for his birthday.
Cheryl and Jim get into a disagreement about Erik Estrada, and Jim tries to prove that the incident that occurred ten years ago was not wrong.
Cheryl believes she's attending a tasteful lingerie party, but is shocked to learn the hostess is selling sex toys and Cheryl buys one, but won't tell Jim.
Jim gets mad when he finds out that his neighbor Julie has been writing children books and basing them about him.
Jim makes his own neighbour cry with complaining about his backyard barbeque, so he ends up taking polite lessons from Andy, in order to become a better person.
Jim believes that Bill, the father of one of Rubys and Gracies classmates is actually his real father that abandoned Jim when he was a child.
Cheryl gives her best to assure herself a spot on the Church Committee, and in order to get that, she forbids Jim to do his annual "Green Man" routine on St. Patrick's day. However, her plans are ruined when she gets arrested.
When Andy stars playing chess with Ryan on a regular basis, Jim is convinced that he is losing his best friend.
When a proud and happy Ryan announces that Dana is pregnant, Jim warns him of Dana's upcoming hormone swings, and ends up dreaming that he is pregnant.
When the family pet guinea pig swallows an eraser, Jim is forced to pay for an expensive operation.
Cheryl and Jim go to a motel in Indiana to celebrate their fifteenth wedding anniversary, but Dana's possible labor and a tornado interfere.
When Cheryl's beloved Uncle Donald dies, Jim takes over housekeeping, but soon starts to suspect that Cheryl is using him.
Cheryl persuades Jim to attend an anger-management class, but he soon learns that getting mad isn't as much fun as getting even.
Andy, Ryan and Jim are stunned when they find out that Dana and Cheryl recently appeared in a Chicks Gone Wild video.
When Dana gets into premature labor, and Ryan isn't able to come and deliver the baby because he is delivering a celebrity's baby, Jim has to be the one to deliver Dana's baby.
When Cheryl and Dana allow Jim and Ryan to take care of the kids and baby Tanner while they are out, things get out of control. Jim takes everyone to the museum and everything goes great until the Tyrannosaurus Rex display ends up destroyed.
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.
After an argument with a claims representative about his bill, Jim's health insurance is canceled, and Jim decides to hide the truth from Cheryl, until she ends up sick and he gets her cold.
Jim decides to toughen up his daughters basketball team and soon turns them from sweet and peaceful to an angry and aggressive basketball team.
Jim's bad softball game advice to Kyle turns to be Jim's worst nightmare when an Ghost of Andy visits him to show him the Adult Kyle's life as a loser.
Andy's new metal detector uncovers Jim's long-lost wedding ring, which causes headaches to Jim, because he bought a fake wedding ring as a replacement a long time ago so Cheryl wouldn't notice he lost it.
Andy and Jim end up in a war after Andy tries to sell him a grill that Jim gave him a few years ago.
After Tim and Cindy Devlin's sudden divorce announcement, Andy starts spending time with Cindy, which turns into a relationship, and an urge for Cheryl and Jim to break them up.
In order to avoid attending another musical with Cheryl, Jim finds a gay man to accompany her.
Cheryl throws Jim an unwanted surprise party for his 50th birthday, which Jim then sabotages, and then later reveals the real reason why he won't celebrate his birthday.
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.
While Cheryl is out of town to take care of her mother, Jim has to take care of their kids, and he receives sympathy from a neighborhood mom. Soon, other moms start helping Jim, and he tells each one that she's the only help in the house.
While Cheryl is still out of town, Jim is having hard time dealing with Ruby's girl problems, so he assigns Dana to help her. However, when Dana tells Ruby to go out on a date with an older guy, Jim if forced to intervene, as he, Dana and Andy end up following Ruby to her date.
When Ruby and Gracie can't seem to stop fighting, Jim is "forced" to read their diaries to determine the cause, only to realize that he needs to give out delicate motherly advice to them, while Cheryl is still away.
When Cheryl returns home for a visit the kids end up occupying her time, so Jim decides to prepare a special date with her at the airport lounge, only to end up mistakenly arrested.
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.
Jim is forced organize a doll-themed party for Gracie while Cheryl is on bed rest, but when Gracie admits that the only reason she agreed to the party was because she wanted to please her mother, Jim decides to turn the party into something totally else.
Jim finds a way to use Cheryl's forgetfulness (a.k.a. "the pregnancy brain") to his advantage by trying to convince her that it was her idea to turn the basement into a media room instead of a room for Ruby and Gracie.
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.
Jim makes a rule he believes to be the perfect cure for children's fights, but when he enters a discussion with Andy, the both end up on the same "tribunal system," fighting to prove who's right.
Andy finally meets the perfect girl, but things get rough when he lets Jim babysit the woman's daughters, who then end up missing while Andy is having dinner with Emily.
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.
Cheryl insists on playing a game that she somehow always wins, but Dana is aware of the fact that Cheryl is cheating.
Jim anxiously awaits for the moment when Cheryl is off bedrest so she'd take over all the chores, but Dana urges him to let Cheryl rest until she goes into labor. After meeting Cheryl's gynecologist, Jim learns that Cheryl was already allowed to be more active, but she didn't tell him.
The Devil himself visits Jim to remind him of the deal they made years ago, when Jim promised to give away his fifth child if the Devil helped him win over Cheryl.
Jim urges Andy to propose to Emily or risk losing her, but when he sees Emily dining with another man, he doubts the wisdom of his advice.
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.
Jim looks forward to a "guys only" weekend with Andy, but when Andy ends up dumped by Emily over a text message and when the guys stumble upon Emily's depressed ex husband, Jim decides to do his best to cheer up the guys and save what's left of their weekend.
Jim is convinced that an old flame wants to get back with him until he realizes that she wants to hook up with Andy, leaving Jim with a bruised ego.
Jim becomes intrigued by Cheryl's raving about a yoga teacher so he decides to try out the class, only to end up impressed by the teacher. Both Jim and Cheryl end up taking separate private classes to relax from their busy family life.
Jim prepares Kyle for his first "date" with Ruby's slightly older piano teacher, Mandy, whom Andy has fallen for and is secretly dating behind Kyle's back.
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.
Andy ends up injured after playing snow football with Jim, so Jim helps Andy make it seem like he had a freak accident because Andy was previously warned by his girlfriend not to play the game.
Jim attempts to look cool in the eyes of Ruby and her friends, until he realizes that he may be undermining Cheryl's authority due to his behavior.
Jim's bad back has him on prescription pain pills which has him in an altered state and opens up an opportunity for the family to share information which usually would upset him.
Jim uses his passion for sports to connect with son Kyle. But sports-challenged Kyle identifies more with fellow sci-fi nerd Andy, forcing a reluctant Jim to dress up as a Cyclops at a sci-fi convention in order to win his son back.
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.
It's Cheryl's birthday and Jim decides to buy her a diamond necklace. But in an attempt to save money, he buys the necklace from Andy's unreliable source and soon learns that it was taken off of a dead woman whose ghost now begins to haunt him.
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.