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.

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.

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.

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.

Michael, who dislikes going out to dinner because it's always an overpriced ordeal, allows Janet to convince him to take the family to a Japanese restaurant.

Michael has problems in the bathroom and needs to have a colonoscopy; he has a dream that his doctor is singer Lou Rawls. Lou Rawls guest stars in an episode that takes a lighthearted but informative look at a serious problem: colon cancer. It's especially acute among African-Americans over 40 - and guess who's 40?

Chaos erupts when Michael tries to get his always-tardy family dressed and out the door to a wedding within just 15 minutes.

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.

Michael's advice about women backfires when Jr. ends up with two dates to a dance. Plus, Jay dreams Michael is having an affair with Janet Jackson.

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.

Michael and Janet's romantic overtures are seen on the Internet after Jr. gets new computer equipment that includes a 24-hour web cam.

Kady has acquired a hamster and Claire has a crush on a boy named Tony. Both developments pose parental challenges for Michael and Jay. The hamster dies. And Michael wishes Claire's new beau would follow suit.

The Kyles face the Tylers in a game of bowling during Star Trek night. The Tyler's daughter tries to charm Junior into throwing the ball and not caring; Junior develops a crush on her.

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.

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.

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 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.

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.

Michael tries to get Claire away from her new boyfriend by befriending him, but things get touchy when she dumps him. Jr. overdoes it in the bathroom.

Michael contends with multiple problems, including a positive pregnancy test, a sad six-year-old and Jr's basketball troubles.

Claire, playing a dare game with Jr. and Kady, eats Michael's piece of pie. Michael's punishment: Let them eat pie (and only pie). Meanwhile, Michael offers to be the dieting Jay's "chubby buddy": He'll eat the same lo-cal food she does. Of course, he doesn't tell her that he plans to cheat.

Michael is stopped by a cop while giving Junior a driving lesson and it seems that Michael's license has expired. So father and son must both take driving tests. Junior gets his license and buys an old clunker instead of what Michael chooses for him.

The anniversary day finally comes and Michael goes out to play golf, leaving Jay devastated at home. Later, she goes out for drinks with her girlfriend Wanda, who insists Jay should confront Michael. Michael pulls off a lavish ceremony for the renewal of their vows. Guest stars Brian McKnight.

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.

Claire drops Tony for zip-code boy 1040-EZ, because her father displayed a liking for Tony.Jr. draws his mother's portrait.