Knowing that Kerry is dragging her feet over breaking up with Kyle, Bridget takes it upon herself to do it for her sister, which only makes matters worse for Kerry. Meanwhile, Cate is offered the position of school nurse by Principal Ed Gibb, and Rory's first day of high school proves embarrassing when he has to hit the showers after gym class.
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 from Principal Gibb (Adam Arkin, ''Chicago Hope''), Bridget and Kerry are convinced that she only took the job to spy on them -- while Rory is ecstatic that his mom might be able to protect him from a school bully. Meanwhile, after Bridget inadvertently spills the beans about Kerry losing her virginity in Europe, a shocked Cate accidentally switches on the school's P.A. system and lets the whole student body in on their ensuing conversation.
Kerry is livid when Bridget unintentionally makes a mockery out of her art project at the mall. But she quickly forgets about Bridget when fellow artist and young hottie Tyler asks her out on a date. However Tyler's intentions may not be completely genuine. Meanwhile, while C.J. finds himself striking out at speed dating, Jim discovers that he's a hit with the ladies-which further humiliates his socially inept grandson.
Bridget and Kerry are ecstatic when Cate hands them the keys to the minivan, except for one provision -- they are responsible for driving Rory wherever he needs to go. But when the girls fail to deliver on their promise to chauffeur their little brother, he takes matters into his own hands and attempts to drive himself -- and wrecks the car in the process.
Kerry doubts Bridget's ability to put together the school's Halloween party as part of her Student Body President duties. Meanwhile C.J. is hired as the party's security guard and sets his sights on catching Rory pulling off a prank, and Jim finds himself under attack by the neighborhood kids when he refuses to hand out candy to the trick-or-treaters.
Bridget is psyched to join the high school tennis team when she develops a crush on Coach Scott (Dan Cortese, ''Veronica's Closet',' ''MTV Sports''). 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.
Everyone in the Hennessy family fears the ringing of the phone when they all find themselves keeping secrets from one-another. Rory refuses to divulge the identity of the student responsible for bullying and beating him up at school, which leads Principal Gibb (Adam Arkin) on a mission to find the culprit and tell Cate; Bridget and Kerry use fake IDs to get into a club, where Bridget meets a cute guy and gives him her phone number -- before discovering that he's a cop (Colby Donaldson, ''Survivor''); Cate doesn't want the family to know that Bridget's tennis coach, Scott (Dan Cortese), is in hot pursuit to get her to go out on a date with him; and C.J. is distracted and forgets to pick up Rory's pain medication, which leads the pharmacist to call the house to find out if Rory's OK
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 -- Principal Ed Gibb (Adam Arkin, ''Chicago Hope''). Meanwhile, while C.J. deep-fries the turkey, Bridget and Kerry spar over pie recipes; Jim disassembles the TV in a shocking attempt to repair it; and Cate finds herself with an insurance adjuster the day after the holiday to find out who was responsible for burning down the garage.
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 his old flame Jackie (Raquel Welch). When he tries to persuade her to reconsider his granddaughter, Jim soon finds himself reminiscing over old times -- and possibly rekindling their romance. Meanwhile, Kerry and Rory discover a secret about C.J'.s past modeling experiences.
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.
To keep C.J. from spending Christmas alone in Las Vegas, the Hennessy household bends over backwards to recreate one of Cate's first holiday memories to entice him to stay. Meanwhile, Rory decides to break up with his wealthy girlfriend when he fears that he won't be able to buy her a Christmas gift worthy of her upper class status.
Cate is shocked to discover that Principal Gibb (Adam Arkin, ''Chicago Hope'') has hired C.J. to be a substitute teacher at the high school. But when C.J. catches Rory cheating on a test, he is torn about reporting it when 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.
While Cate finds herself becoming jealous of Principal Ed Gibb's (Adam Arkin, ''Chicago Hope'') new girlfriend, Cheryl (Pamela Anderson), C.J. is asked by Ed to help tutor Cheryl for her G.E.D.s -- and finds himself unwittingly being hit on by her. Meanwhile, Rory feels awkward after Cate accidentally interrupts him during a private moment.
After sending an email to former college flame Matt (Ed O'Neill) 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 - then she begins to question if his rebel lifestyle is just a front.
When Cate and C.J. discover that Kerry has been e-mailing Bruno -- the boy she had a fling with in Europe -- they secretly try to snoop in her computer to find out what the two have been up to. But unbeknownst to them, Bruno is in the house and hidden in the attic by Kerry, while Bridget tries her best to talk her little sister 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 about gambling.
Cate's alleged antics at Kerry's volleyball game threaten to make her team forfeit the match. Meanwhile, C.J. has a crush on Kerry's volleyball coach (former Pro Beach volleyball player Gabrielle Reece), and Bridget becomes upset when one of her friends begins dating her ex-boyfriend.
Following a viewing of ''Freaky Friday'' in which she fell asleep, Cate awakens to find that she and Bridget have switched bodies, as have C.J. and Grampa along with Rory and his hamster. While Kerri sits back and enjoys their predicament, Bridget begins enjoying having her mother's voluptuous body while Cate can't stand her being in her daughter's body all of the time.
Valentine's Day finds C.J. in a predicament when he commits to two different Valentine's Day dates - Principal Gibb's ex-girlfriend, Cheryl (Pamela Anderson), and Bridget and Kerry's uptight math teacher, Mrs. Krupp. Meanwhile, Bridget's excitement over being elected to the court of the Valentine's Day dance -- with a chance to be crowned Queen of Hearts -- quickly turns to shock when she discovers that Cheryl is also in the running.
C.J. is shocked and delighted when his biological father (Danny Woodburn, recurring on ''Seinfeld'' as Mickey Abbott) andacirc;andeuro;' a motivational speaker and ''little person'' andacirc;andeuro;' reveals himself for the first time to his wayward son. But Jim doesn't trust the man and thinks he may have ulterior motives for the visit. Recording artist Ruben Studdard makes a cameo appearance.
After turning down Bridget's request to throw a ''harmless'' after-prom party in a hotel room, Cate decides to throw a school- sanctioned party at the house andacirc;andeuro;' 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.
Officially a full-time teacher, C.J. is overjoyed to finally get access to the teachers' lounge. But he soon finds himself being bullied out of the room by the school's overzealous Home Ec instructor, Mr. Edwards. Meanwhile Rory wants to impress a girl, so Bridget and Kerry take it upon themselves to give him a full-fledged makeover.
After Principal Gibb (Adam Arkin, ''Chicago Hope'') and Cate fall asleep at the house while watching a movie, the family catches them and falsely assumes that the two are having a relationship. Meanwhile, Bridget, Kerry, Rory and C.J. are forced to go ice-fishing with Jim in order to spend quality time with their grandfather - but unbeknownst to them, Jim would much rather be left alone and is forced to keep up a happy fagade.
After C.J. discovers that Cate may be starting a clandestine relationship with Principal Gibb, he blabs it to Bridget. An angry Cate gets even by having Gibb put C.J. in charge of the detention of students on Ditch Day, and C.J. gets even by detaining Bridget. Meanwhile, because she is stuck in detention and can't complete the ditch day prank herself, Bridget convinces Kerry and Rory to steal the rival school's mascot. Nicole Richie (''The Simple Life'') guest stars as one of Bridget's fellow detainees.