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
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
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
Michael and Janet try to spice up their date nights by taking samba lessons, but their instructors arouse jealousy
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
Claire drops Tony for zip-code boy 1040-EZ, because her father displayed a liking for Tony.Jr. draws his mother's portrait
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
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
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 and it sparks a rivalry
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
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
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
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
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
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
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
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
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 quick 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
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 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
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
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