As Cate decides to go back to work as a nurse, Paul undertakes the responsibility of watching the kids.

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.

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.

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.

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.

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.

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.

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.

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.

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 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 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.

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.

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.

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.

Bridget is horrified when Cate is asked to fill in as the sex ed instructor in her daughter's class. But Cate is in for a shock when she tries to answer a student's written question about being pressured to have sex -- and realizes it may be from Bridget. Meanwhile, Paul and Kerry are too embarrassed to look each other in the eye after watching a foreign film together that contains a sexually explicit scene.

Cate receives a phone call that Paul had collapsed and died in the grocery store. Later that evening, Cate's parents arrive to help them through their grief.

Cate is unprepared for the diverse reactions exhibited by Bridget and Kerry on their first day back to school since their father's death. Meanwhile, Jim tries his best to be helpful by making some questionable home improvements to the Hennessy home.

While Cate plans to raise the family spirits with a special Thanksgiving dinner, Rory takes it upon himself to be the man of the house by looking after Bridget and Kerry.

Rory steals a police dog when he hears about CJ's glory days of stealing his old school mascot, but Cate is shocked when the dog finds marijuana in Kerry's backpack. Meanwhile, Bridget gets brought home by the police for not wearing a helmet on her boyfriend's motorcycle after Cate telling her she has to.

In need of a tutor to boost her grades, Bridget hires Jeremy, hoping to make her chance of getting into a good college better. Meanwhile, Kyle treats Kerry to an very un-corporate Valentine's Day celebration. Rory gets pointers about the perfect gift for his new girlfriend Missy. Jim sends C.J. on an errand to get a special drug in Canada.

Bridget decides to make a move on her tutor but discovers that he may have his sights set on her debate team opponent. Meanwhile, after accidentally setting fire to C.J.'s van, Jim is not-so-thrilled when Cate forces him to share his basement room with him.

After being told that she's fickle when it comes to relationships, Bridget is afraid that she may end up hurting Jeremy's feelings when her ex-boyfriend returns to town. Meanwhile, Kerry is outraged and plans revenge when provocative dancing has been banned from the high school formal, which is being chaperoned by Cate and Jim. C.J. partners with Rory to broadcast school scandals over the internet.

On the advice of the family therapist, Cate is encouraged to pursue her dream of becoming a singer. Meanwhile, C.J. and Jim find themselves trying to bond in a bar when Cate encourages C.J. to take his grandfather out after he is dumped by his wife in a letter. Kerry angers Bridget by dying her hair blonde after she complains that the romance is fading from her relationship with Kyle.

Cate sends Bridget and Kerry to their grandmother's house for a visit after the Hennessys decide against vacationing at the family cabin. But while on their road trip to grandma's, the girls are shocked to find Cate at their father's favorite saloon with a mysterious stranger. Meanwhile, Kerry makes Rory's life miserable when she discovers that he has a crush on her friend, Rachel.

Upon discovering Cate in the arms of Artie, Bridget and Kerry decide to blow off their planned trip to their grandmother's and take to the open road to sort out their feelings. Meanwhile, Rory continues to pine for Rachel Sharpe, who confesses her true feelings for him.

Kerry gets in the art program in Europe in the summer, but Cate forgot to submit her medical records in time. Together they appeal to principal Gibb. C.J. falls for Missy's big sister Sissy and Gramps for a woman he has a car accident with.

Knowing that Kerry is dragging her feet over breaking up with Kyle, Bridget takes it upon herself to do it for her sister. Meanwhile, Cate is offered the position of school nurse and Rory's first day of high school proves embarrassing when he has to hit the showers after gym class.

After Cate accepts the position of school nurse, Bridget and Kerry are convinced that she only took the job to spy on them. Rory is ecstatic that his mom might be able to protect him from a school bully.