In the premiere episode, six-year-old Ruby suffers separation anxiety during her first week of kindergarten and won't let Cheryl leave the classroom. Jim boasts the situation just needs the emotionally strong heart of a dad. But when he finds he doesn't have the willpower to leave Ruby at school in tears, and the teacher insists he leave, Jim comes up with his own questionable solution. He transfers Ruby to a new school where he sits with her all day. To top it all off, he keeps this a secret from Cheryl to protect his pride.
Tired of rushing to have sex in whatever few moments they can spare, Cheryl arranges a romantic getaway to the Bahamas. Dana will babysit the kids, leaving Cheryl and Jim free to rekindle their romantic flame. Cheryl even convinces Jim to abstain from sex for three weeks, until they get to the Bahamas. The trip falls apart, though, when Dana realizes that she cannot babysit the kids due to a business trip.
Meanwhile, Andy builds a tree house for Grace and Ruby, and gets a little carried away.
Cheryl is upset by the death of her cat, Mr. Feeney. She asks Jim to give the cat a proper burial, but he sticks the cat in the freezer so he can watch a football game. Cheryl discovers the cat, and she is upset by Jim's insensitivity.
Jim persuades Dana to buy a gift for Cheryl for their tenth anniversary. Dana chooses a beautiful charm bracelet, with little trinkets symbolizing the special moments in Jim and Cheryl's relationship. Cheryl loves the gift from Jim, until she discovers that Dana was the one who really bought it. She is upset that her husband doesn't know her well enough to buy her a nice gift. Cheryl says that she'd like whatever Jim bought her, as long as it came from the heart.
Just to spite his wife, Jim comes home with a replacement gift - a giant-screen TV. To his surprise, Cheryl actually loves the new gift.
Jim sneaks Gracie out for some Halloween trick or treating, though Cheryl has forbidden her to go, and Andy is convinced he's being stalked by a former girlfriend when he receives a series of creepy phone calls and packages.
Jim sets Dana up with a guy so perfect that even Cheryl falls for him.
When Andy decides Dana is responsible for his inferiority complex, he asks her to join him in his therapy - but she falls for his therapist; Jim and Cheryl disagree about letting the kids to have their own TV; Jim admits to riding his motorcycle, breaking a promise he'd made to Cheryl earlier; and Ruby innocently divulges a secret of Cheryl's, exposing a broken promise of hers to Jim.
Jim can't tear himself away from a Thanksgiving Day bowling tournament, though Cheryl and her guests anxiously wait to start dinner.
Andy brings tension to dinner when he announces that, like his new girlfriend, Alicia, he's become a vegetarian. Meanwhile Dana is frustrated when her dream date, a renowned physician, can't seem to commit to more than five minutes.
Cheryl is hurt when her mother gives Dana a cherished heirloom for Christmas, and Ruby and Gracie think Andy, decked out as Santa, is the real thing.
While watching a Bears game, Jim blurts out profanity which is repeated by a little friend of Ruby's and Gracie's, then later by both girls. Jim denies uttering it, but gets busted.
When Ruby is hired for a cookie ad, Jim sees an opportunity for a lucrative modeling career for his daughter.
Cheryl decides to go behind Jim's back and loan Andy $1,000 for a downpayment on a new condo.
When Cheryl has a revealing photo of herself taken as a Valentine gift to Jim, he proudly shows it to all his friends.
When Cheryl reminds Jim that she beat him at racquetball years ago, he claims he was only letting her win to gain her affections, so Cheryl challenges him to a no-holds-barred re-match.
When Jim develops high blood pressure, Cheryl tries to create a stress-free environment.
Jim and Cheryl's quiet night on the town turns into a fiasco, while Andy is cajoled by Dana into doing her delinquent taxes.
Jim is compelled to prove his worth by buying his kids an expensive gift after he learns that Dana makes more money than he does.
Jim loses a receipt to return a defective DVD player and Cheryl berates him for it — until she discovers that she's the one who lost it.
Jim tries to revisit his wilder days when his old buddy, Danny (guest star Dan Aykroyd ), returns to town.
Jim and Andy leave Ruby and Gracie with one of several moms they met at a park while they go to the movies — then they forget who they gave them to! Meanwhile, Cheryl decides to spend the day with Dana at the movies and sees Jim there with Andy and Kyle.
When Cheryl goads Dana into admitting Jim has planned a surprise party for her, a furious Jim cancels the party. A guilt-ridden Cheryl then decides to throw a party for him on her birthday instead — but Jim is too busy bowling with Chicago Bears football star Brian Urlacher to show up.
Cheryl and Jim clash when he breaks a promise to save a digital photo she values.
Jim claims women aren't capable of getting a good deal on a car, and prophetically, when Cheryl helps Dana buy a new car, it turns out to be a lemon. Dana begs Jim to use his macho influence at the dealership to help her, but instead he allows sexy sales manager Gretchen (Cindy Crawford) to talk him into trading the family van in for a sports car — without consulting Cheryl.
Cheryl is dying to be "couple friends" with Ted and Janet, some new neighbors. Against Jim's wishes, she sets up a dinner date with the couple. After a pleasant evening and the guests are gone, Jim and Cheryl manage to overhear — on a baby monitor that Cheryl loaned her guests — a conversation Ted and Janet are having about them. Later the conversation goes from innocuous to intimate, but Jim and Cheryl can't tear themselves away from the speaker. So they have to pretend everything's normal at their next get-together with the Janet and Ted (and Ted's 'alter ego,' "Little Winston"), until Jim's big mouth gets him in trouble once again.
Jim's pizza delivery boy moves in with him and Cheryl after the boy's father kicks him out of the house because of his dream of doing standup comedy.
Jim is upset when Cheryl's stuff takes over the entire house, leaving him with no private place of his own.
Cheryl is concerned that Jim is being a bad influence on the kids when he takes them to a Bears game and they witness him punching a spectator; but Cheryl's disparaging remarks about her body image put her equally at fault as an example.
When Dana is picked to be a bachelorette on the reality series The Bachelor, Jim gives her a little advice on how not to be herself.
The charismatic new preacher at Cheryl and Jim's church holds a grudge against Jim for a childhood dodge-ball incident.
When Jim and Cheryl are caught fooling around after hours on the set of their kid's Thanksgiving play, Jim tries to find a way to reinstate Cheryl in the good graces with the PTA.
Cheryl and the kids are invited to a neighbor's annual Christmas party, but Jim, who is feuding with the neighbor, isn't invited.
Country singer Brad Paisley guest stars as Dana's new boyfriend, an amazing musician who can get Jim the gig of his dreams — once Andy is out of the way.
Jim treats Cheryl to a romantic weekend with money he knows was mistakenly credited to his card.
Cheryl and Jim try to play matchmaker to a cop and his female partner (Dan Aykroyd and Laraine Newman), and Jim and Cheryl's memory of how they met doesn't mesh with the recollections Andy and Dana have, on a special one-hour episode.
Cheryl and Jim try to play matchmaker to a cop and his female partner (Dan Aykroyd and Laraine Newman), and Jim and Cheryl's memory of how they met doesn't mesh with the recollections Andy and Dana have, on a special one-hour episode.
Cheryl isn't very supportive of Jim's latest invention, a flatulent doll named "Gassy Gus."
When Cheryl gets sick on the day of Ruby's birthday party, Jim is stuck trying to entertain a house full of little girls.
When Jim and Cheryl run into his old girlfriend, Jim worries that Cheryl may find out the truth about his past when she invites the woman to dinner.
When Cheryl is mugged while shopping, Jim goes into protective overdrive.
A childhood buddy of Jim's who "has it all" hires Jim to design his expensive new home. A resentful Jim doesn't want to take the job at first, until he learns the guy wants something that "belongs" to Jim — Cheryl.
Jim stands up to Dana's caustic boss — and gets her fired — and Andy has trouble delegating the arrangements for his birthday party.
Jim is torn between holding a nervous Cheryl's hand through her two-hour dental surgery or meeting his hero — blues legend Bo Diddley.
Jim and Cheryl are conflicted when their new friends turn out to be obnoxious — but are also able to get free Bears season tickets and discounts on hot tubs.
Jim refuses to spend money for a new dryer for Cheryl, but he secretly spends money for pricey sports memorabilia online, which Cheryl discovers when she simultaneously bids against Jim for a Chicago Bears helmet for his birthday.
When Gracie adopts an abandoned bird, the household cries fowl about the annoying addition to the family.
Dana pretends to be Ruby's mother to gain the interest of a single dad she met in the park.
When Cheryl's recently widowed mother, Maggie, introduces her fiancÈ to the family, Cheryl and her siblings are wary of their whirlwind romance.
On a family trip to Vegas, Cheryl secretly plans a reunion with Jim and his estranged sister, Roxanne (Jennifer Coolidge), on the special, one-hour season finale.
On a family trip to Vegas, Cheryl secretly plans a reunion with Jim and his estranged sister, Roxanne, on the special, one-hour season finale.
Jim tries to prove his competence at running errands for Cheryl, but soon realizes that he's becoming her fetch-it boy. And Andy, in the meantime, thinks that flashing his wedding ring around will somehow transform him into a "chick magnet."
When Jim's son becomes attached to a Packers football, Jim tries to turn him into a Bears fan instead.
Jim wrestles with his conscience after he cheats at a church fundraiser bingo game.
When a girlfriend of Cheryl's gets an expensive necklace from her husband, Cheryl presses Jim to do the same for her.
Jim encourages Gracie and Ruby to earn money for new scooters by opening a lemonade stand, but he doesn't anticipate fierce competition from the neighbor kid's stand — and his parents.
Jim tells Ruby's teacher that Cheryl is illiterate in order to lessen his struggling daughter's homework load.
Dana falls for a guy just like Jim — but she denies the similarities.
Gracie and Ruby have nightmares after Jim secretly takes them to see a scary movie.
Jim creates an imaginary friend to avoid going to a couple's baby shower with Cheryl.
Cheryl cajoles Jim into attending a couples cooking class, which turns into a disaster, so she lets Jim pick out the next couples activity — paintball.
Cheryl feels very much taken for granted as she prepares Thanksgiving dinner this year, especially when she gets stranded on the roof retrieving a tablecloth Jim had fashioned into a Halloween ghost — and no one notices her absence until she unhooks the satellite. To make amends, Jim tells her that he, Dana and Andy will prepare the holiday feast. He assumes the mere gesture will be enough, and so doesn't bother to actually make the dinner. Unfortunately, neither does Cheryl.
Cheryl caters to Jim's every whim to make amends for a big fight they had the night before — except Jim doesn't remember the fight at all.
Dana admits to Cheryl that she can't afford to buy Jim a Christmas present, so Cheryl lets Dana put her name on one of the presents she bought for him. Dana innocently picks out Cheryl's big present to Jim, but when Jim is thrilled with the gift, Dana is ready to take all the credit for it.
The Devlins return to haunt Jim and Cheryl when they decide to put a bid on the house across the street.
Dana falls for the Reverend Pierson after he sets her up with a promising job lead.
Jim tries to convince his nervous friend, Danny (Dan Aykroyd), not to back out of his wedding plans with Laraine (Laraine Newman).
Cheryl tries to impress her braggart cousin, Mindy (Rachel Harris), by telling her that she is the singer in Jim's band.
Dana's first task in her new ad agency job is to cast the perfect TV family for Disney's cruise line. Cheryl and the kids get the job, but for the role of "dad" Dana's new boss picks a handsome actor over Jim.
Dana's first task in her new ad agency job is to cast the perfect TV family for Disney's cruise line. Cheryl and the kids get the job, but for the role of "dad" Dana's new boss picks a handsome actor over Jim, on a two-part story arc.
Gracie's recent misbehavior spree makes Jim think she's lying when she claims her new Gameboy was a gift from a new friend.
Jim's sister, Roxanne (Jennifer Coolidge), shows up on his doorstep — pregnant — and Andy discovers he may be the father.
Andy resents a rich, bossy client (Nana Visitor), then dates her.
Cheryl ask Jim to use his truck to transport a giant paper-mâché grizzly bear the girls made for "spirit week" to their school -- except Jim just lost his truck in an arm wrestling match and, in a gesture of macho pride, refuses to ask for it back.
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.
Tensions rise when Cheryl discovers that Dana is dating one of her ex-boyfriends, Doug, who dumped her without explanation 15 years ago. When Jim learns that Doug has season tickets to the Cubs, bygones are bygones and he's suddenly Doug's best friend. But when Doug, characteristically, ends up dumping Dana — and Jim too - they all vow to get to the truth about Doug.
During a heat wave, Jim, the kids, Dana, Andy and Andy's new girlfriend sneak into a vacationing neighbor's pool to beat the heat -- despite Cheryl's initial protests. But then Cheryl starts sneaking over to the pool by herself and hides this from everyone else.
Cheryl asks Jim to get a vasectomy after a pregnancy scare. Jim reluctantly agrees, but chickens out right before the procedure. When Cheryl lavishes him with praise for his unselfish move, he can't admit to her that he didn't go through with it, on the season finale.
Immediately following the 100th episode, a special half-hour retrospective episode takes a hilarious look at Cheryl and Jim's botched anniversary moments from years past.
Cheryl wants Jim to give up his vices so he can get her pregnant.
When Cheryl's surprise romantic evening for Jim cuts into his planned TV boxing match, he dispatches her by getting her drunk.
Jim gives Andy an old barbeque, then turns around and wants him to pay for 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.
Jim worries that Kyle is becoming a sissy when the boy insists on wearing a Cinderella costume for Halloween.
Jim feels hurt when Ruby invites Andy to the father-daughter dance instead of him.
Cheryl's mother, Maggie (Kathleen Noone), 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 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 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 (Tom Arnold).
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, an overly superstitious sports fan, believes that his former wacky neighbors, the Devlins, bring luck to the Bulls when they watch the game with him.
Jim buys a nanny-cam to spy on a sitter he didn't want Cheryl to hire, but instead catches Cheryl on tape hiding money from him. When Cheryl finds Jim's tape, she buys a nanny-cam to spy on him.
To make Cheryl feel desirable, Jim fakes a jealous rage in a restaurant over Cheryl and the waiter. He then teaches Dana's date how to fake jealousy to impress Dana. But the plan backfires when Dana comes to view her new beau as paranoid and possessive.
Cheryl thinks men who aren't afraid to cry are sexy, but when Jim watches a movie she rented and bursts into tears, Cheryl is surprisingly turned off by his overly sensitive behavior.
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.
Closet ballroom dancer Jim teaches Andy how to dance so that he can impress sister Dana at her wedding.
When Cheryl wants to see an opera, Jim fixes her up with an elderly widower whose interest in Cheryl may be more than platonic.
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 see that his newly deceased buddy Beltzman is going to be buried with a prize baseball card he once stole from Jim.
In order to spend more quality time together, Jim and Cheryl turn back the clocks to make their kids go to bed earlier.
Certain that he will win the annual hot dog eating contest, Jim is humiliated when instead he loses to a petite woman (Suzy Nakamura), and his problems are further compounded when Andy decides to date the female champion.
Cheryl hosts a boring bachelorette party for Dana, which inspires Jim and Andy to bring her out for a real night out on the town. But when a well meaning Jim warns Dana about the trappings of marriage (i.e. no sex ever again!), a drunken Dana runs off to find Ryan at his medical convention to call off the wedding. Cheryl manages to save the day when she goes after Dana and calms her fears.
Cheryl and Dana think they have cause to worry when Dana's fiancé, Ryan (Mitch Rouse) wants to race fast cars and Jim wants to take up skydiving, on the landmark 100th episode of According to Jim.
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 sneaks Kyle out of his first day of kindergarten to go see a Cubs game -- against Cheryl's wishes.
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.
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 who 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 (Kathleen Noone), visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection.
When Jim and Cheryl preview a sex education video to be shown to children at Ruby’s school, they discover that the boy in the video is Jim.
Jim and Cheryl squabble during a ceremony to renew their wedding vows after Cheryl allowed Gracie and Ruby to get their ears pieced even though Jim had adamantly forbidden it.
On his birthday, Jim accuses Cheryl of habitually choosing gifts intended to change him instead of to please him.
Cheryl and Jim get into an argument about Erik Estrada, and Jim sets out to prove Cheryl wrong about an incident that occurred with the actor ten years ago.
Cheryl thinks she’s attending a tasteful lingerie party given by Andy’s new girlfriend, Bernice, but is shocked to learn the hostess is selling sex toys – and Cheryl buys one, but won’t tell Jim.
Jim discovers that his neighbor has written a series of children’s books in which she models the series’ grumpy old man on him and chronicles the long-standing feud between them.
Jim decides to reform and become the model of polite diplomacy after making a neighbor cry.
Jim believes that the father of one of Ruby’s and Gracie’s classmates is his father who abandoned his family as a child.
Cheryl urges Jim to behave on St. Patty’s Day and forego his annual law-bending “Green Man” routine so she can assure herself an appointment to the church committee. Her chances are nevertheless diminished -- not because of Jim, but for her own arrest for public lewdness.
Andy starts to play chess with Ryan on a regular basis and a jealous Jim assumes Andy is no longer his best friend.
When an ecstatic Ryan (Mitch Rouse) announces that Dana is pregnant, Jim advises him on how to avoid the pitfalls of Dana’s upcoming fluctuating hormones. Then Jim dreams that he is pregnant.
Jim thinks that Cheryl has been spoiling her son Kyle for way too long, and Jim's idea is to help Kyle throw the perfect punch when in self defense. However Jim's idea goes haywire when Kyle gets suspended for repeatedly hitting the school bully.
When Jim claims that men should not let woman feminize them, he ends up on a talk show. Then he goes to Dana's co-ed baby shower to prove his point.
Jim feels like a guinea pig in a test of humanity when the family pet needs a costly operation, and he's the one holding the purse strings.
Jim and Cheryl's plans to mark their 15th anniversary in Indiana are undone by Dana's labor pains and an impending natural disaster.
When Cheryl's beloved Uncle Donald dies, Jim takes over housekeeping, but soon starts to suspect that Cheryl is using him.
A raging Jim accidentally backs into a police car while chasing down a guy who blasts his car stereo daily down his street. When arrested, Jim opts for anger management classes in lieu of paying the fine -- which thrills Cheryl, who is convinced Jim has IMS, Irritable Man Syndrome.
Jim and Ryan are shocked to learn that images of Cheryl and Dana have surfaced in a "Chicks Gone Wild" video.
Dana goes into labor early, and since Ryan is unable to get home in time to deliver the baby, Jim must fill in.
Dana and Cheryl hesitantly entrust Ryan and Jim to watch the kids and baby Tanner while they have a girls' night out. But Jim sneaks the brood into the museum after hours to see the dinosaur exhibit, and their shenanigans result in the destruction of the Tyrannosaurus Rex display.
Dana and baby Tanner stay with Jim and Cheryl while Ryan is away, but Jim complains the baby's crying keeps him up all night, so Cheryl urges Jim to stays over at Andy's. The guys end up enjoying some male bonding while Cheryl and Dana secretly enjoy their pampering girl time without Jim around. All is perfect -- until Ryan returns.
Jim's health insurance is canceled after he argues with a claims representative about his bill, but he doesn't tell Cheryl. When Cheryl gets a cold, Andy convinces Jim to buy tropical fish antibiotics at a pet store to prevent Cheryl from going to a doctor. The pills work and she improves. But when Jim catches Cheryl's cold and takes the same fish pills, he has an allergic reaction. Then Cheryl discovers the truth about the health insurance.
Jim coaches his daughters' wimpy, non-competitive basketball team and turns them into tough, aggressive winners.
Jim's repeated bad advice to Kyle during a softball game is thrown back in his face when the Ghost of Andy gives him a glimpse of a future Kyle as a loser because of Jim's failed attempts to help his son on that fateful day.
When Andy buys a metal detector, he unearths Jim's wedding ring -- which has been lost for over a year. Unbeknownst to Cheryl, Jim has been wearing a fake ring all along, hoping she wouldn't notice.
Andy's attempt to sell a grill that Jim gave him a few years ago results in a wildly destructive tug-of-war between the two.
When Tim and Cindy Devlin crash Gracie's birthday party, they announce they're getting divorced. Soon thereafter, Cindy and Andy become an item -- resulting in Jim and Cheryl plotting to break the two up.
To avoid attending another musical with Cheryl, Jim finds Cheryl a gay male friend to accompany her.
Jim is turning 50 and doesn't want a birthday party, but Cheryl, not believing him, throws him a surprise party -- which he deliberately sabotages. Later Jim confesses to Cheryl about being humiliated at his 13th birthday party -- an event that scarred him for life.
Jim is dismayed to learn that Cheryl has joined a dinner party club. When he grumbles that he'd like to meet the moron who invented women, God suddenly appears to defend himself. If Jim thinks he can do a better job, he's welcome to try. But Jim's new-found power backfires when Cheryl and Dana become crasser versions of himself. Then, when Andy asks God to make men more like women, Jim and Andy are transformed into overly sensitive, girly men.
Cheryl can't flirt her way into a reservation at a hot new restaurant, and she begins to worry that her beauty has faded. So Jim cooks up a scheme to cheer his wife up. When he starts to forge suggestive notes from the handsome water delivery guy, Cheryl's mojo returns. But, as things start to heat up between Cheryl and Jim, he wonders if Cheryl's really thinking about Jim or the water delivery guy.
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.
Jim and Cheryl feel an ease of their marital woes after having a food fight. That is, until Andy seeks revenge on Jim for some past pranks played against him by his children.
Jim uses the female neighbors to help keep the house clean and care for the kids, while Cheryl is away taking care of her mother.
Jim is having trouble playing the role of both parents while Cheryl is out of town, taking care of her mom and reassigns the "mommy' duties to Dana after Ruby tries to talk a little "girl talk" with him.
Jim reads his daughter's diaries in hopes of discovering why they bicker so much, which informs him that as one daughter is coming of age and the other is jealous because she hadn't done so already.
While Cheryl visits, the kids demand all her free time, and a planned rendezvous with Jim at the airport, never quite gets started.
While Cheryl is still away in Florida, Jim gives a charity drive all their old baby clothes and furniture. But when Cheryl calls and announces she is pregnant, Jim scrambles to retrieve the belongings.
Jim is forced to host Gracie's doll-themed birthday party while a pregnant Cheryl is on bed rest.
When pregnant Cheryl has memory problems, Jim takes advantage of the situation and builds a "man cave" in their basement instead of a child's room.
Jim finds out that Andy has forgotten to use a gift certificate that he bought him for his birthday. Not wanting the money to be wasted, he uses it on himself. All is well until Andy remembers he has the gift certificate and invites Jim to eat with him.
Jim suggests a tribunal to sort out the kids differences since they keep arguing all the time. But the system comes back to haunt him when the children suggest their parents do the same after Jim and Andy have a dispute.
Andy feels he may lose Emily after Jim offers to bring her daughter's to a concert with Ruby and Gracie.
Now that their relationship has lasted the customary six weeks, Andy is afraid Emily will leave him as all his previous girlfriends have done. Dana puts him under a hypnotic spell in order to get to the source of his relationship problems and discovers that he causes his own break-ups due to low self-esteem. While under, Dana adds a boost of confidence to his persona which ends up backfiring when he begins to flirt with every girl he sees while on his six week anniversary celebration with Emily.
While a very pregnant Cheryl is on bed rest, she insists on playing her usual game night, a game in which she never loses...and Dana knows why, because Cheryl cheats.
Jim is creating a long list of chores for Cheryl to take over from him when she's off bedrest, but Dana tells him that the doctor ordered Cheryl stay in bed until she goes into labor. When Jim runs into Cheryl's gynecologist at the super market and learns that she's actually been told she should be active now, he confronts Cheryl, who admits that going off bedrest could induce labor and she wants to prolong her pregnancy just a bit longer to enjoy Jim and the kids before the twins are born.
The Devil come to collect on a deal Jim made with him years ago when he was courting Cheryl - that he would give up his fifth child if the Devil would make Cheryl fall in love with him.
Cheryl finally smaps from loss of sleep after being up all night with the twins, so Jim has to take care of the children When he realizes Jonathan's special Christmas snowman blankie has gone missing he, immediately blames the older kids who, out of guilt, comply with Jim's request to complete the household chores. When Jim realize the blanke was with him the whole time, he and Cheryl enjoy the best of both worlds--kids doing the chores and sleeping babies, but not for long.
Jim has to find Cheryl a new best friend after her sister Dana moved away.
After Jim and his band win a contest and have the opportunity to play in front of child pop diva Jami McFame.
But after hearing her intimidating ego mouth off, Jim tries to set her straight.
Jim convinces Andy to propose to his girlfriend, Emily, before he loses her. But when Jim catches Emily having dinner with another man, he questions the wisdom of his own advise.
To earn some money for Christmas gifts for his five kids, Jim goes behind Cheryl's back and gets the twins parts in a Steve Guttenberg movie.It wasn't until after Jim had devised the plot and the director had cut the twins hair that he learns what the meaning of Christmas is all about.
Andy and Jim are excited to have a "guys only" weekend at Andy's fiancee's cabin in the woods. However Emily breaks up with Andy via text message, and then the guys encounter her depressed ex-husband in the cabin. So Jim goes to great lengths to cheer up his old friend and his new friend in hopes of salvaging the weekend.
When Jim runs into and old flame, Victoria, who happens to be the owner of a new restaurant that he Andy are trying, he becomes convinced she wants him back. But when Jim discovers she wants to date Andy, his ego is bruised and he has a tough time letting go.
When Jim realizes that Cheryl has taken a strong interest in yoga with a male instructor she raves about, he becomes jealous and tries to figure what the hype is all about. He joins her class realizing he, too, enjoys moments of Zen with Cheryl. But peace and tranquility are replaced by rage as Jim and Cheryl take yoga classes behind each other's backs to escape the chaos of 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.
Jim convinces Andy to play snow football even though Andy's girlfriend, Mandy, warns him against it. Now injured, Andy has to hide his injury from Mandy, so Jim stages a freak accident for Andy in his home.
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.