The rivalry between Cate and Maggie comes to a boiling point when Maggie gets a sexy, new makeover and gives Bridget a water bra as a gift. Tensions between the Hennessy sisters mount when Kerry and Kyle begin dating, while Bridget's popularity takes a nosedive after she dissed her friends for Donny. Paul becomes concerned when he finds an empty pregnancy test kit.
Having learned that her sister Maggie is having marital problems, Cate is nevertheless not too thrilled when Paul invites Maggie to stay at the house. Meanwhile, Paul and Cate are impressed with how mature Bridget has become after they agreed to let her go out with neighbor Donny Doyle, who is home from the Naval Academy. Bridget and Kerry wonder if Kyle has ulterior motives when he befriends Rory.
After reluctantly inviting socially inept neighbors Fred and Mary Ellen Doyle and their kids over for dinner, Paul and Cate are shocked when the entire Hennessy clan is asked to take part in the Doyles' daughter's wedding. Meanwhile Kerry neglects to inform Bridget that geeky Donny Doyle has grown up to be a hunk, and Rory takes a part in a play as a cross-dresser in order to meet girls.
For a health class assignment, Bridget and Kyle have to take care of a sack of flour as if it were a baby. Kerry and Rory bake cookies for the Great American Bake Sale to help put an end to childhood hunger in America.
Bridget and Paul are surprised to find themselves in similar situations when they are both alienated in their social circles. But they devise a plan to settle the score, leading Paul to crash a poker game with Tommy to get closer to boss Nick, and Bridget trying to break up ex-boyfriend Kyle and her nemesis Jenna.
Paul's job as parental guardian becomes more of a full-time position when Cate is up for a promotion and has to spend more time at the hospital. After Paul introduces Rory to baseball card collecting, Rory trades the cards for something not exactly associated with the sport.
While vacationing in Florida at Cate's parents' home, Paul and Cate catch Bridget and Kerry on the news partying with a group of Spring Breakers. But the news runs archival footage that features a young Cate letting loose in a bar. Meanwhile, a jealous Paul meets Cate's college boyfriend Byron and Rory befriends an elderly gentleman whose stories about World War II turn out to be more fiction than fact.
Kerry devotes her school video project to sister Bridget to illustrate the hypocrisy that life is much easier for the beautiful people. But when Bridget discovers that the video makes her look shallow, she takes Paul's advice to enrich her life by taking up tennis again.
When Paul is asked by race car driver Carter Tibbits (Jason Priestley, "Beverly Hills 90210") to write a book about him, Paul brings the family to Tibbits' mansion to meet the driving legend and his sarcastically dry-witted butler, Cody (Robert Guillaume, "Benson," "Sports Night") -- who used to be Carter's crew chief. But a misunderstanding leads Rory to steal a photo from Carter's room, and it's Paul who's under suspicion when a security camera catches him trying to return the item.
After a party at Tommy's house is broken up by the police, Paul chastises his friend and unwittingly volunteers to host the next one. But when the party gets out of control too, the kids think of him as a cool parent, while the neighborhood parents think he's just as unreliable as Tommy.
Bridget takes the car and follows her older boyfriend, drum instructor Ben, to his college dorm.
Bridget defies the rules of the house after Paul forbids her from going out on a date with Ben, her college-age drum instructor. Meanwhile, Kerry is mad at Cate when her ex-boyfriend confesses that he thinks her mother is pretty.
After discovering that boyfriend Kyle kissed Kerry at a party, Bridget gives her sister the silent treatment which is anything but quiet for Paul. But real life merges with fantasy when Paul has a dream that lands him in familiar territory, showing Kyle as a swinging bachelor living with Paul's two beautiful daughters in an apartment straight out of the 70s.
After Kerry and her boyfriend break up, Paul tries to cheer her up by getting Bridget to take her little sister with her to a party. Meanwhile, Paul and Cate try to discover what is hidden in Rory's secret box.
Paul and Cate are shocked when they are called into the principal's office and informed that Bridget wants to skip her college prep classes in order to become an esthetician. Meanwhile, Paul is so impressed with Kerry's sketches of The Incredible Boring Woman that he gets the principal to print them in the school newspaper.
When a proud Paul lets thirteen-year-old Rory go out on his first date, Bridget and Kerry accuse him of unfairly changing the rules because they were never allowed to date at that age. Kerry is shocked when Bridget receives a higher score then she did on a state aptitude test.
Paul tries to find perfect gifts for the family to make up for last year's Christmas fiasco. Kerry finds a stray dog during the holidays. Cate is overjoyed when she is asked to sing a solo at the church's midnight service, but fears that seeing her family there will make her nervous.
Paul becomes quick friends with his new editor Nick when he discovers they both are married fathers of teenage girls. But Paul soon learns that they both have the reputation of being an overprotective psycho dad. Meanwhile, Paul wants to make Thanksgiving a family affair, and forbids Bridget and Kerry from inviting their boyfriends.
When no one can agree on where the family vacation should take place, Paul challenges the Hennessey clan to give up their bad habits for a week and the winner gets to choose the vacation spot. But the family's vices soon get the better of them, and secret collaborations and clandestine alliances threaten to foil the contest.
After Paul convinces Bridget to tell Kyle the truth about her date with another boy, Kyle breaks up with her. Meanwhile, Kerry's first date turns out to be a dream, but she is devastated when the boy doesn't call her back.
In an effort to win back the love and respect that his daughters used to show him when they were young, Paul turns to a parenting book for some quick advice. But when Bridget and Kerry discover Paul's teaching tool, they try to use it to their advantage to get their father to let them go to a rock festival.
Paul seems to be the only one looking forward to a family Halloween, as Bridget, Kerry and Rory make plans to spend the spooky evening away from home and with their friends. But Paul's wish to relive the past by having the family get together for one last Halloween campout in the old treehouse may turn out to be the biggest nightmare of the evening.
Bridget is ecstatic when the cheerleading squad has an opening for a new member. But after telling Kerry that she is not cut out to be a cheerleader, Bridget is completely dumbfounded when her sister tries out and is chosen for the team. Meanwhile, Paul tries in vain to wean Rory off video games and introduce him to the world of books.
A sports-struck Paul lets Bridget do whatever she wants when she starts dating Travis, star basketball player and son of baseball legend Steve Smith. Meanwhile Kerry resents the fact that Paul still thinks of her as a little girl.
Bridget takes drastic measures when an overprotective Paul keeps coming up with excuses to delay her from taking her driver's test. Meanwhile, after convincing a less-than-confident Kerry that she has the talent to enter an art competition, Paul is shocked and Kerry is devastated when her submission is rejected.
After seeing how much money Bridget spends on keeping up with the latest fashions, Paul tells her to go out and get a job to learn how to be fiscally responsible. But when she lands a job at a trendy mall clothing store that offers its workers a 40% discount, Paul and Cate begin to worry that she may not be learning the true value of a dollar.
Paul is left home alone with the kids while Cate is at a seminar on the day of the big Michigan/Ohio State football game. But much to Paul's dismay, the game soon takes a backseat when Bridget is accused of shoplifting and Kerry gets upset over her latest cause.
As Cate decides to go back to work as a nurse, Paul undertakes the responsibility of watching the kids.
