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.

Jim plans a surprise party for Cheryl's birthday, but gets angry and cancels it when Dana spills the beans. To make it up to him, Cheryl plans a party for him... but he's too busy bowling to show up.

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.

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.

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.

Cheryl wants Jim to give up his vices so he can get her pregnant.

Jim tries to blackmail Dana when he finds out she’s having erotic dreams about him.

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.

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.

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." Thanksgiving-themed episode.

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.

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.

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 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.

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.

It's Halloween, and Cheryl has forbidden Gracie to go trick-or-treating. However, not wanting his daughter to miss out on the fun of the halloween spirit, he sneaks her out anyway. Meanwhile, Andy becomes convinced that he's being stalked by an ex-girlfriend.

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.

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?

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.

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.

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.

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.

Jim gets mad when he finds out that his neighbor Julie has been writing children books and basing them about him.

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.

Cheryl and Jim try to play matchmaker to a cop and his female partner , 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.

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 has a run-in with an old friend from his wild and crazy days who is now a cop. Jim sets out to prove he's not an 'old married guy' by staying out all night and partying. Unfortunately, this has bad consequences for both of them...

The Devlins place a bid on the house across the street from Jim and Cheryl, to their dismay.

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.

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.

Cheryl isn't very supportive of Jim's latest invention, a flatulent doll named "Gassy Gus."

Cheryl persuades Jim to attend an anger-management class, but he soon learns that getting mad isn't as much fun as getting even.

Jim sets Dana up with a guy so perfect that even Cheryl falls for him.

Andy, Ryan and Jim are stunned when they find out that Dana and Cheryl recently appeared in a Chicks Gone Wild video.

When Cheryl gets sick on the day of Ruby's birthday party, Jim is stuck trying to entertain a house full of little girls.

Jim guilts the older kids into doing household chores after Jonathan's special blanket goes missing.

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.

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.

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.

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.

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, on the Season Finale.

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.

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.

Cheryl protests when a heat wave sends the family sneaking into a vacationing neighbor's pool -- until she starts sneaking over on her own.

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 is shocked to learn that his recently deceased friend will be buried with a rare baseball card he stole from Jim.

Dana pretends to be Ruby's mother to gain the interest of a single dad she met in the park.

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.

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.

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.

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 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.

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.

Cheryl and Dana think they have cause to worry when Dana's fianc - wants to race fast cars and Jim wants to take up skydiving.

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.

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 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 takes umbrage at being replaced as the father in a promotional shoot for a cruise line.

Jim's sister, Roxanne, shows up on his doorstep, pregnant, and lets Andy believe he's the father.

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.

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 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.

Andy resents a wealthy client, but then decides to date her.

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.

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.

While out for dinner and a movie, Jim loses a parking spot, and later loses Cheryl when he can't let go of it.

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.

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 develops a friendship with Dana's new boyfriend, despite the fact that the guy dumped Cheryl years ago.

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.

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.

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.

Jim creates an imaginary friend to avoid going to a couple's baby shower with Cheryl.

When Andy stars playing chess with Ryan on a regular basis, Jim is convinced that he is losing his best friend.

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.

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.

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.

Dana's first task at the ad agency is to cast the perfect TV family for a Disney cruise commercial. Cheryl and the kids get the job, but Dana's boss replaces Jim with a handsome actor in the role of "dad."

Andy and Jim end up in a war after Andy tries to sell him a grill that Jim gave him a few years ago.

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.

In order to avoid attending another musical with Cheryl, Jim finds a gay man to accompany her.

When Dana, Cheryl's sister and best friend, moves away, Jim realizes he must find Cheryl a new friend as soon as possible.

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.

When Cheryl's beloved Uncle Donald dies, Jim takes over housekeeping, but soon starts to suspect that Cheryl is using him.

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.

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.

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.

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.

Cheryl and Jim go to a motel in Indiana to celebrate their fifteenth wedding anniversary, but Dana's possible labor and a tornado interfere.

Gracie's recent misbehavior makes Jim think she is lying about a friend giving her a new video game.

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 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 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.

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.

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.

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.

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 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.

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 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 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.

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.

Cheryl and Jim clash when he breaks a promise to save a digital photo she values.

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.

Dana and Jim both covet their reverend - she for romance, he for the pastor's prowess at bowling.

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.

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.

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.

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.

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.