After Michael admits liking Claire’s boyfriend, Tony, she dumps him. The poor kid is devastated, and since Michael likes him so much he decides he’s going to help Tony win Claire back – specially after seeing her new boyfriend, Jason (or “1040 EZ” as he likes to call himself). The results aren’t good, so Michael has a heart-to-heart with Claire. He explains to her that Jason isn’t good to her, and any men who are with her should treat her like the princess she is. Since the talk doesn’t show any results either, Michael decides to act like he likes Jason and see if that makes Claire dislike him. Luckily, Claire comes back to her senses and gets back together with Tony. Meanwhile, Jay refuses to admit she looks like Jr.’s drawing of her. Instead, she believes she looks more like Halle Berry.
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The Kyles are leaving for their family vacation on Hawaii, but instead of taking only one flight straight to the island, Michael thought it would be a good idea to make a quick tour around the country, so they make stops at New York, Chicago, Denver and other cities before they get to Hawaii (two days later). When they finally get there, Michael's luggage gets lost and they're forced to take a master suite because their reservation expired. While Michael wants to make it a romantic and resting trip, Jay wants to get to know place, and drags the entire family on a historical tour – except for Michael, who chose to sleep in. The kids are sick of the tour and go back to the hotel. Jr. tries to meet women and buys a book on how to talk to women subliminally, while Michael keeps scaring away any guy who lays his eyes on Claire.
Michael and Janet decide to go out on a romantic dinner, leaving their kids all alone. Claire and Jr. fight over who'll have to stay in the room babysitting for Kady, but Claire lets her brother get out of the duty, after all it's not often he gets a date. Jr. has a memorable night on the beach with Leilani, a native girl. Kady and Claire decide to spend their times on the hotel's spa, while at the dinner table Jay and Michael both struggle to say no to the temptations they met – a female underwear model and a male chest/abs model. When they go back to the hotel, they find their three kids resting in peace. Kady and Claire are glowing like never before, and Jr. has the biggest smile on his face. With all three sleeping deeply, Michael and Jay decide to extend their night at the beach, celebrating their second honeymoon.
A mad scramble ensues when Michael finds out that the family's flight home from Hawaii leaves much earlier than he thought, but matters are complicated when a love-smitten Jr. insists on staying with his new love, Leilani. Meanwhile Kady refuses to leave without her beloved doll, Little Pippy, and Claire has to go to extremes to keep her parents from finding out about her exorbitant hotel charges
Tired of the same dinner-and-a-movie routine, Jay convinces Michael to take dancing lessons to spice up their relationship. At first reluctant, Jay's argument that wins Michael over is that he better go to those lessons or else she'll shut down "pantyville". When they get there, only more problems waits for Michael. The samba instructor is all over Jay, which makes him so jealous he has the guy deported. The new instructor, however, is a very attractive woman who is all over Michael, making Jay jealous now. They decide to quit the samba lessons after all and spice up their marriage in their own way. Meanwhile, Claire's accepted in the cheerleading squad, but won't believe she only got in for her looks and not for her talent – which is none.
While making Claire's bed, Jay finds her diary hidden under the mattress. She can't resist the temptation of reading it and is quite shocked to learn that her daughter is thinking about taking the next step with Tony. She has a heart-to-heart talk with Claire, about the consequences of pursuing hr hormonal desires. Meanwhile, Michael is scheduled for an appointment with the eye doctor even though he insists there's nothing wrong with his sight (doesn't matter than he can't even read the paper without squishing his eyes). He decides to have Jr. drive him there so he can test his driving abilities for an upcoming date with a girl. When he comes out of the doctor's office, Jr. is gone, and Michael tells him that he disappointed him big time, and if he can't trust Jr. to be there for his family, then he might want to consider moving out. And all Kady wants to do is play hide-and-seek.
After Michael admits liking Claire's boyfriend, Tony, she dumps him. The poor kid is devastated, and since Michael likes him so much he decides he's going to help Tony win Claire back – specially after seeing her new boyfriend, Jason (or "1040 EZ" as he likes to call himself). The results aren't good, so Michael has a heart-to-heart with Claire. He explains to her that Jason isn't good to her, and any men who are with her should treat her like the princess she is. Since the talk doesn't show any results either, Michael decides to act like he likes Jason and see if that makes Claire dislike him. Luckily, Claire comes back to her senses and gets back together with Tony. Meanwhile, Jay refuses to admit she looks like Jr.'s drawing of her. Instead, she believes she looks more like Halle Berry.
Jay volunteered to be the; Director for Kady's kindergarten class play, but due to illness she is forced to step away from the production, leaving it all on the hands of Michael – for the children's salvation, because Jay was way too competitive, even arguing with their teacher over the quality of their last show. Michael allows the children to make any changes they want on Shakespeare's "Romeo and Juliet", and the result is a very successful – and very weird – play.
Sick and tired of listening to their kids’ fights, Michael and Janet act like they are fighting themselves so Jr. and Claire can see how annoying it is and quit it. But the three Kyle children get the wrong idea and think their parents are splitting up, and try their best to bond them and end the fake fights.
Michael's sister Kelly is coming over for the weekend, which freaks Jay out because every time Kelly comes over she overstays her welcome and always gets on Jay's nerves. This time is no different, with Kelly constantly throwing on Jay's face that she is fatter than her, a worse cook than her and even tries to make her look like a bad singer, even though Jay can sing wonderfully. Things heat up when Kelly brings up Sharon, Michael's old girlfriend and Kelly's best friend. The two women get into an argument and it's up to Michael to break them up. He pulls it, and Kelly and Jay finally get along. But for how long?
Michael decides to help Junior on his women approach techniques, seeing that his son has absolutely no clue on how to behave around women. His advice consists on primarily having women say "really?", which is the key for a successful approach. When Jr. tests Michael’s advice on one of Claire friends, he's surprised that it works, and even gets the girl to agree on going on a school dance with him. But Jr. was just testing her so he could ask the hottest girl on school out, which he does (and she accepts, on a move to make her ex-boyfriend jealous). Claire's friend is crushed, and Michael now has to teach him how to apologize properly to a woman. Meanwhile, Jay freaks out about her dream of Michael and Janet Jackson having an affair.
Feeling that she has no space and time of her own due to home duties, Jay decides to paint. The result is a portrait of Michael based on Michelangelo's David, which makes Michael feel a little bit "diminished". They start an argument over it, which ends on Michael finally agreeing on letting Jay show her work at a friend's art gallery – with a "big" change, that is. Meanwhile, Michael renews acquaintances with old buddy Steve, while the kids are encouraged to develop their artistic abilities as well. Claire designs clothes, Kady plays the piano and Junior, like his mother, decides to paint.
Michael's old friend Tommy is coming over and Michael is very excited because he and Tommy used to compete for everything. But his excitement soon turns into awkwardness when Tommy shows in on a wheelchair and Michael doesn't know how to act with the situation. Tommy decides to take advantage of that until they have a talk in which Tommy asks Michael to treat him like he used to, because despite the wheelchair he's the same guy that used to race Michael for anything. Meanwhile, Claire is caught shoplifting and gets grounded for it. When she confronts Kady about who put the nail polishers in her purse she feels so guilty she confesses to their parents that Claire didn't do it. The punishment? She will no longer be treated like a baby.
Jay decides to attend an "Open Your Heart" seminar for struggling couples, even though she and Michael are happier than ever. Her excuse is "prevention", but Michael warns her not to try fixing something that isn't broken. At the seminar, they are teased against each other and stop talking to one another. It takes Kady suffering an accident at school for them to realize how important communication between them really is. Meanwhile, Michael wants his children to learn the value of money and tells Jr. to start his own business selling monkeyfish like he. Jr., instead of the monkeyfish, decides to get 100% refunds on the clothes Claire buys with a 40% discount at the store she's working. When Jr. gets caught, Claire gets fired and Michael punishes him by making he wear the clothes he wanted refund.
Michael (aka: Chief Bald Eagle) is recruited to camp out with Kady and her friends and teach them Native American lore. Meanwhile, Clare and "the new Tony" plan to stay out all night themselves: they're plotting to sneak out to a "rave."
Michael wants some time alone in the house and makes a deal with Jay for her and the kids to get out of the house. But of course it doesn't come as easy as he hoped. He has to pay for Claire to agree on going to the mall and is forced to watch The Little Mermaid with Kady for the hundredth time. He switches the movie to Gremlins, which scares the death out of the poor girl, and when the power goes off Claire freaks out about losing her entire work on the computer. In the end, the power failure ends up bringing the Kyles closer together.
Jay nominates Michael for the "Small Businessman of the Year" award and he assumes he's going to win it (especially after a golfing buddy on the organization's board tells him: "If my vote were the only one that counted, you'd be a shoo-in"). Meanwhile, Claire helps herself to items from Jay's makeup bag once too often.
As a very impressed Michael sees it, his son's girlfriend, Vanessa is an absolute prize: "She's beautiful, smart, personable and polite... you guys have nothing in common," he tells Jr. But there's something about her that rubs Jay the wrong way. Elsewhere in the courtship department, Kady's similarly smart and personable gentleman caller is a budding piano prodigy named Franklin. As for Claire, all she's courting is a severe case of nerves: the PSATs are coming up and her face has broken out in hives.
After walking in on Jr. and his girlfriend having sex on his bed, Michael decides that he and Junior can no longer live under the same roof and throws his son out. Feeling sympathetic for her baby, Jay opposes to Michael's attitude, but at the same time agrees the boy needs a severe punishment. She had Jr. stay on a tent in the backyard until she can cool things down with Michael, who only realizes he might be estranging his son for good after Vanessa has a woman-to-woman talk with Jay. Michael lets Jr. move back, remembering that he once was in the same position as Jr.
Michael and Jay are asked to serve jury duty together. Michael's elected foreman and wants to move on the trial quickly so he can get home to watch the "Godfather" marathon on TV. But Jay won't vote in guilty because she thinks there has to be a debate first. Thanks to that, Michael ends up missing the marathon, and has to rent the videos to catch up with the movie. At the video store, he meets an insurance salesman whom he mistakes for a mobster, and is convinced that the mob is after him due to the case. The case ends up being dismissed before they can vote, and Jay is disappointed that Michael wouldn't back her up but has her revenge when Michael acts like a fool.
When Jr and Claire find a lost wallet containing $500, it's time for a session of "family court" to decide who gets the money. Meanwhile, Claire's boyfriend Tony induces her to become a vegetarian.
Claire has taken her driving permit, but Michael won't lend her the car because he doesn't think she can drive very well. Nevertheless, Claire steals the car keys thinking if she goes out really quickly while her parents are gone they will never notice. Unfortunately, she drives by them on her way to meet her friends, and Michael decides to teach her a lesson on the Michael Kyle style: stealing the car and making Clare feel guilty about it. She goes to Junior for help, and they call the police reporting the stolen car. Michael ends up in jail due to the mix-up, but he and Clare end up getting along after everything is cleared up.
Jay gets mad at Michael after finding a photo of an attractive former girlfriend among his things. Franklin has trouble admitting that his little sister Aretha is an outstanding singer.
Jay decides to spend more quality time with Michael - by watching him play golf. Meanwhile, Jr., who only wants to go to college because Vanessa's going, asks Franklin for help with the application essay.
Michael and Jay panic when Claire reveals that she and Tony have decided to have sex. Her parents try by all means to change their minds and stop them, unsuccessfully. When the day and time comes, their find out Claire has sneaked out of the house and panic. Claire and Tony show up a few minutes later, and just when Michael is ready to kill him, Tony reveals that they didn't do anything. Just when they were about to do it, he opened the drawer on the hotel room's nightstand and found a bible, which he took as a sign from God. But he doesn't have to know that every hotel has a bible.
Claire comes home with the exciting news that she was invited to senior prom. Jay is excited about it and volunteers to chaperone at the dance, in order to keep Claire safe from her date, a senior quarterback. But Jay's exaggerated excitement makes Claire feel uncomfortable, especially when her parents are crowned queen and king of the prom. Michael tells Claire that she shouldn't be upset about it because Jay never attended her own prom as she was giving birth to Junior that night, and so Claire lets her mom enjoy her moment. Meanwhile, Junior falls into another one of Michael's plans once he tries to teach the kid a lesson about money management and ends up turning his car the exact opposite of Junior's plans.
Jr.'s graduation is coming up, and he breaks the news to his family that he wants to go to college. At first shocked, Michael decides to help him make a good interview, but his anxiety and lack of good sense makes him look like a complete moron. He even tries to bride the interviewer, when he's finally asked to leave Jr. alone. The kid does reasonably well. A few days later a letter arrives at the Kyles, saying that Jr. got accepted but has to take summer school classes. Meanwhile, Clare wears a blond wig to call her parents attention, thinking she has been forgotten now that Jr. is on the spot. And Franklin applies to the soon available son spot on the Kyle family.
Junior finally graduates, and his parents give him a trip to Japan as a gift – and as a way to separate Junior and Vanessa, who are planning on moving in together and getting married as soon as they start college. Both Kady and Clare admit their sadness on Junior leaving, and Michael and Jay feel proud of having raised a semi-successful child. They go out to relive some of their memories and when they come back late at night they find Junior and Vanessa sitting in the kitchen. He's decided not to go to Japan anymore. Vanessa is pregnant.