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.

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.

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". Michael renews acquaintances with his old buddy Steve, while the kids are encouraged to develop their artistic abilities aswell. Claire designs clothes, Kady plays the piano and Junior writes some bizarre poetry

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 good. 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.

When Jay insists that Michael buy her a present for ""Sweetheart's Day,"" a reluctant Michael comes up with a scheme to base the price of Jay's gift on her attitude towards him at a particular moment. He shares his plan with Jr., Tony and Franklin, hoping that they will follow the lead, but the only lead is straight to trouble.

Michael reluctantly accompanies Jay on a meditation weekend, where he has trouble following the rule of silence.

Jay is ready to graduate from college, but a series of events ruin her appearance.

Jay is trying to get rid of some old clothes, so after Michael opposes to that she and him make a deal that everything that is not worn by the end of the week has to go. Meanwhile, Junior is trying to learn how to play the guitar and his friend convinces him to smoke pot. Kady gets angry at Claire for avoiding her.

The Kyles are leaving for their family vacation on Hawaii, but instead of taking only one flight straight to the island, Michael books a 43-hour flight to Hawaii with several layovers in order to save money. Plus, Michael chastises Janet for packing too many clothes.

While Jay is away at a seminar, Michael hires a maid, Mrs. Hopkins, to look after the family. Mrs. Hopkins fulfills their every need and want to a sweet perfection, including homemade ice cream, an immaculately clean house and handmade outfits for Claire. When Jay comes home, she appreciates Mrs. Hopkins' attention to every detail, but begins to feel that perhaps she has taken over just a bit too much.

Junior fakes an A in algebra while his family, not fooled by the charade, fakes a celebration. Meanwhile, Claire blackmails Junior because she had caught him red-handed forging his report card.

While making Claire's bed, Jay finds her diary hidden under the mattress. She can't resist the temptation of reading it and learns that her daughter is thinking about becoming sexually active. Michael is scheduled for an appointment with the eye doctor even though he insists there's nothing wrong with his sight; he asks Junior to drive and Michael reprimands him for his poor driving skills.

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 on 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 a ""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.

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.

Michael advises Jr. that it's ok to spend some time away from Vanessa and the baby, but his advice misfires when Jr. invites Jay along to their all-male poker game. Michael decides, in turn, to crash Jay's all-female book club, where they're discussing the latest book by Angeline Boudreaux.

Jr. is finally ready to propose to Vanessa, but every time he tries to do so, something interrupts him, including Michael and Jay -- who are preparing to compete against each other in a karaoke competition.

The same day Michael realizes he can't fit into his favorite pair of vintage jeans, he runs into an old high school friend, the muscular Daryl (Terry Crews), who doesn't look any older than when Michael last saw him. He enlists Darryl's help to get him back into shape and, in the process, becomes obsessed with looking fit and buff. Meanwhile, Franklin fails his first test and fears that Kady will no longer accept him.

Michael suspects the family is less than truthful about certain matters. Junior gets some tattoos; Michael annoys Kady.

Michael hires an attractive girl to tutor Junior in math and later regrets his actions. Also, Jay doesn't like the direction her relationship is going with Claire, who is turning into a typical teenager.

The family goes out to eat at a Japanese restaurant. Once there, the Kyles must share a table with an incredibly annoying family, the Tylers. Michael feels like he's being ripped off at every turn; things get out of control between the two families and even the restaurant employees. The two families have been enemies ever since.

Finally in Hawaii, 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. Michael and Janet are pursued by two attractive strangers; Claire goes on a shopping spree.

Michael doesn't take it well when he loses to his teenage son at basketball. Meanwhile, Claire thinks the best way to attract boys is to have bigger breasts, so she buys a padded bra, much to the dislike of Jay who punishes her for doing so.

Michael decides to let the kids live a rule-free life, but on the condition that they do everything for themselves; including cooking and paying for their own phone calls.

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 Michael to fill the void; he allows the kids to do whatever they want.