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.

Everyone fears the ringing of the phone when they all keep secrets from each other. Rory refuses to divulge the identity of the student responsible for beating him up at school. Bridget and Kerry use fake IDs to get into a club, where Bridget gives her phone number to guy, unaware that he's a police officer. Cate doesn't want the family to know that Coach Scott tries to get her to go out with him. C.J. is distracted and forgets to pick up Rory's pain medication.

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 sending an email to former college flame Matt to see how he's been doing over the years, Cate becomes fed up with the unreasonable demands of her family and locks herself in her room for some alone time. But she's shocked when Matt shows up at her window and whisks her off to re-live some adventurous, old times.

When Cate and C.J. discover that Kerry has been e-mailing Bruno, they secretly try to snoop in her computer to find out what the two have been up to. Unbeknownst to them, Bruno is hiding in the attic, while Bridget tries her best to talk Kerry out of doing something she may regret. Meanwhile, Jim discovers Rory's clandestine poker game and decides to deal himself in to teach Rory and his friends a lesson.

Bridget is ecstatic when she learns that tennis scouts from Princeton are coming to her school to watch her play for a possible scholarship. But when Bridget's school forbids her to play because of a poor grade, Cate has to decide whether to use her clout as school nurse to help her daughter out. Meanwhile, Jim promises a nervous C.J. that he'll give up his room if he can spend one night alone in the attic.

After turning down Bridget's request to throw an after-prom party in a hotel room, Cate decides to throw a school- sanctioned party at the house which totally embarrasses her kids. Meanwhile, Kerry tries to make a political statement by inviting a girl to the prom, and Rory is overjoyed when a hot senior asks him to the dance.

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

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 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.

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.

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.

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.

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.

Kate gives Bridget and Kerry the keys to the minivan, provided they drive Rory wherever he needs to go. But when the girls repeatedly fail to drive him, he attempts to drive himself, wrecking the car in the process.

Bridget is psyched to join the high school tennis team when she develops a crush on Coach Scott. But her infatuation soon turns to disgust when she learns that Scott has a crush on Cate. Meanwhile, Kerry and Rory begin to question the authenticity of Jim's war stories while rummaging through his war chest.

While Cate finds herself becoming jealous of Principal Ed Gibb's new girlfriend, C.J. is asked by Ed to help tutor Cheryl for her GEDs -- and finds himself unwittingly being hit on by her. Meanwhile, Rory feels awkward after Cate accidentally interrupts him during a private moment.

Cate is shocked to discover that Principal Gibb has hired C.J. as a substitute teacher. When C.J. catches Rory cheating on a test, he is torn about reporting it as Cate tries to persuade him to look the other way. Meanwhile, when Bridget breaks her leg because of Kerry's blunder, she makes her little sister's life a living nightmare.

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.

The kids question Cate's motives when they return from their summer getaways and discover that she has bought a new bed and changed her hairstyle. Meanwhile, after traveling through Europe over the summer, Kerry met and had a fling with a boy - which leaves Bridget jealous and Kerry wondering what to do about boyfriend Kyle; new high school Student Body President Bridget is convinced even further that life is a popularity contest after taking a trip to Washington, DC over the summer; and after a depressed Jim fails to win back the affections of his wife in Florida, Rory attempts to help him quit smoking -- which is complicated by Jim's discovery that C.J. was responsible for their irreconciliation.

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.

Kerry doubts Bridget's ability to put together the school's Halloween party as part of her Student Body President duties. C.J. is hired as the party's security guard and sets his sights on catching Rory pulling off a prank. Jim finds himself under attack by the neighborhood kids when he refuses to hand out candy to the trick-or-treaters.

While the family prepares Thanksgiving dinner for Cate to give her some much needed time off, she's left with nothing to do until she brings home an unexpected guest while on an errand. While C.J. deep-fries the turkey, Bridget and Kerry spar over pie recipes. Jim disassembles the TV in an attempt to repair it.

After Bridget is turned down for a role in a sports car commercial, Jim discovers that the head of the modeling agency who rejected her is an old flame. When he tries to persuade her to reconsider his granddaughter, Jim soon finds himself reminiscing over old times. Kerry and Rory discover a secret about C.J.'s past modeling experiences.