Paul's perfect day of watching a big game on TV uninterupted is ruined when Bridget is caught shoplifting.
Paul's plan to make Briget get a job to teach her the value of a dollar may have backfired when she gets a job at a mall clothing store.
Bridget tries to get around Paul's procrastination of letting her take her driver's test while Kery is devasted when Paul encourages her to enter an art contest and she loses.
Paul eases his dating restrictions on Bridgit when she starts dating a baseball legend's son while Kerry resents how Paul treats her like a child when she to start dating too.
Kerry wins the spot on the cheerleading squad, much to Bridget's chagrin and Paul tries to teach the value of books over video games to his son.
Paul's idea of a fun family Halloween spent as a camp-out in their old treehouse is spoiled by his children's independence and desire to spend it with their freinds.
When he thinks he has lost his daughter's resepect, Paul resorts to a self help book to get closer to them but when they get wind of his plan, the press their advantage.
Bridget is dumped by Kyle when Paul convinces her to tell the truth about a date she had with another boy while Kerry's perfect date is spoiled when the guy never calls her back.
Paul holds a contest where each family member gives up a bad habit for a week and whoever holds out the longest chooses the where they take the family vacation.
Paul makes fast friends with his new editor, bonding over their teenage daughter woes and finds more than enough common ground when Paul witnesses his new friend's family dynamic. Also, family strife escalates when he won't let his daughters bring dates to the family Thanksgiving dinner.
After screwing it up the previous season, Paul set out to find the ultimate Christmas gifts for his family and Cate is torn between the thrill of being asked to sing solo in the church choir on Christmas and the fear of doing it in front of the family. Keery finds a stray dog that has a penchant for destruction.
The girls accuse Paul of having double standards when he laxes his dating rules for Rory's first date. Also, Kerry is baffled when Bridgit gets a higher score on their SAT's.
Bridget makes a decision to forego her college prospects for a career as an asthetician. Also, Paul is impressed with Kerry's cartoons and he convinces the school principal to print them in the school paper, npot realizing that the drawings are of the principal herself.
When Kerry breaks up with her boyfreind, Bridget is forced by Paul to let her tag along to a party. But the plan backfires when Kerry and Bridget's boyfreind Kyle share a kiss.
Paul and Cate must deal with their bickering daughters after Bridget aims her fury at Kerry for kissing Kyle. Paul ends up dreaming about a sitcom starring his two daughters who live with Kyle as characters and a set eerily close to "Three's Company."
Paul's good intentions go awry when he hires a handsome college boy to teach Bridget to play the drums and she defies the house rules by dating him. Also, when Kerry's ex-boyfreind makes the comment that he thinks Cate is attractive, Kerry takes her anger out on her mom.
Bridget sneaks away to be with her new crush, the drum instructor Paul had hired, driving to his college for a rendevous. Meanwhile, Rory tries to find an alternative to reading a book for a report.
Paul is upset when his co-worker Tommy hosts a party attended by the kids and it gets broken up by the police. Paul decides to chaperone his own party and ends up losing control as well but is labeled a cool dad in the process.
Paul is asked by a famous race car driver to author his biography and invites the whole family to his mansion. Rory ends up taking a photo from the house and Paul get's busted when he tries to secretly return it.
Bridget is the subject of Kerry's video project, which attempts to show how much easier life is for "beautiful people." When Bridget sees how shallow her life appears, she takes up tennis, only to get her nose broken.
While the family is vacationing in Florida, Bridget and Kerry are caught partying on the evening news. But before they can be punished, the television station runs archival footage of a young and wild Cate partying in a bar. Meanwhile, Paul becomes jealous of a man that Cate used to date.
When Cate has to spend more time at the hospital, Paul's parental duties at home increase. Also, Rory learns about baseball card collecting.
Bridget and Paul try to settle the score with their respective social circles after they find themselves alienated from them.
For a school project, Bridget has to be the mother of a sack full of flour.
Fred and Mary Ellen Doyle, Paul and Cate's socially inept neighbors, invite the entire Hennessy family to take part in their daughter's wedding.
Cate's sister, Maggie, who is having marital difficulties, comes to stay at the house. Meanwhile, Bridget goes out with neighbor Donny Doyle, who is home from the Naval Academy.
Cate's sister gets a sexy makeover and gives Bridget a water bra as a gift. Also, Kerry and Kyle begin dating and Bridget upsets her friends by spending all her time with Donny. Plus, Paul finds an empty pregnancy test kit.