Bridget finds her popularity waning because of her exclusive, long distance relationship with Donny, while Kerry's social status skyrockets because of her relationship with Kyle. But Bridget's eyes begin to stray when she meets Damien (Paul Wesley) — a sexy new boy at school. Meanwhile, as she waits for the results of her pregnancy test, Cate is stunned and angry when Paul, Bridget, Kerry and Rory seem more concerned about how the baby could disrupt their lives than the blessed event itself. In
Cate teaches sex education at Bridget's school and gets suspicious when she reads a submission where a girl's older boyfriend was coming from Maryland and she felt pressured to have sex. Bridget tries to cover it up by saying that this was a girl from Maryland, Lara O'Neal (which turned out to be made-up; Bridget herself was the one who wrote the question). Meanwhile, Paul is worried about Kerry after they saw a French movie with a sex scene in it.
The Doyles are sending a video postcard to Donny, which they let Bridget have a part in. However, Bridget breaks up with Donny on the video, which leads to a feud between the Hennessys and the Doyles. Upset, Donny hitchhikes all the way to the Hennessys in the back of a pig truck to win Bridget back; however, Bridget has still not broken up with her other boyfriend, Damien. Meanwhile, there are reports of eggings and toilet-paperings all over the neighborhood. Paul tries to come up with names fo
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.
Two weeks have passed since Paul died, and the kids begin to get special treatment when they return to school. While Kerry decides to lay low, Bridget tries to move on like it never happened.
Cate sees that Rory is now hesitant to try out for the basketball team because Paul had been helping him practice. Cate tells him that his father wouldn't have wanted him to quit. The newspaper Paul worked at is sponsoring a scholarship dinner in his name for students majoring in journalism, and Bridget gets distracted while watching television, and accidentally wrecks a collage that Kerry had made of Paul for the dinner. When it's announced at the party that Rory made the team, Rory angrily sto
It's the first Thanksgiving without Paul. Cate's mother visits, and manages to get along well with Jim. Bridget and Kerry plan to sneak out to a party instead of staying with the family. Rory feels that, now he's the man of the house, it's his job to assume Paul's role of being against every guy his sisters date, not to mention the carver of the turkey — which he does with clumsiness, inexperience and a lot of humor, which in the end helps the family to make it through the first of many mileston
Bridget plays the role of Anne Frank in the school play, which makes Kerry jealous, since all she does is background work. At first, Bridget is the same non-serious girl, which frustrates Kerry even more since she feels Bridget doesn't deserve the role. Cate sees this too, so she gives Bridget The Diary of a Young Girl, because she thinks it might help her, which it does – Bridget suddenly becomes a serious, focused girl and gets a better understanding of the role she is going to play. Rory gets
Bridget gets a job as a lifeguard at the local YMCA, which prompts Cate to enroll the whole family (to Bridget's chagrin). However, Kerry is unimpressed with a group of young blonde girls who idolize Bridget, while Jim punches another man for making comments about Bridget. Elsewhere Rory has an unexpected pubescent experience in a yoga class. Note: This is the first appearance of David Spade as C.J.
Cate's nephew C.J. stops by the Hennessy household to pay his final respects to Paul. C.J., however, can't resist getting into trouble when he gives Rory advice about kissing a girl, which lands him in detention, and then takes the blame when Kerry, while driving with just a learner's permit, dents Cate's car while driving Bridget on an errand.
Rory steals a police dog when he hears about C.J.'s glory days of stealing his old school mascot, but Cate is shocked when the dog finds marijuana in Kerry's backpack. Cate thinks Kerry's using drugs because of her father's death, but it's really just teenage rebellion. 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 a Valentine's Day special, Bridget is forced to partner with geeky Jeremy (Jonathan Taylor Thomas) in Science class, and ends up falling for him. Meanwhile Kyle decides to take Kerry's stance against a commercialized Valentine's Day, only for him to surprise her with a romantic gift she wasn't expecting.
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.
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-bad boy boyfriend, Damian, 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, and Jim falls for Ms. McKenna (Tatum O'Neal), a member of the high school's PTA
The family therapist (Peter Bogdanovich) encourages Cate to pursue her dream of becoming a singer (her "skydiving", as the therapist puts it). In turn, Cate encourages C.J. to end his feud with Jim, so he takes him to the bar where Cate is singing. Bridget accidentally dyes Kerry's hair blonde. Katey Sagal (Cate) performs the song "Daddy's Girl" from her 2004 album "Room".
Kerry gets a job at an embarrassing fast food restaurant at the mall to make money for her trip to Europe. Grandpa wants to pay his fair share at Cate's house and also gets a job there. However, Kerry might have to fire her grandfather for treating customers with disdain at the fast food restaurant. C.J. has a job as a security consultant at the mall, and he takes it very seriously. He then busts Bridget for going into the wrong movie theatre at the mall, interrogates her and tries to ban her fr
After Bridget, Kerry and Rory vote against going on vacation to the cabin at the lake, Cate orders Bridget and Kerry to fly out to visit Grandma Laura in Sarasota instead of attending the Maeve Festival, believing the festival to contain "sex, drugs, and rock and roll". However, on their way to the airport in Kyle's car, the girls spot Cate hugging a mysterious stranger at their dad's favorite bar. Meanwhile, Rory, even though he is dating Missy Kleinfeld, develops an interest in Rachel Sharpe.
Upset and confused over their mother's behaviour, Bridget and Kerry decide not to go to their grandma's, and instead take a road trip to sort out their feelings. Along the way, they pick up C.J., who has been attacked by a group of women at the Maeve Festival. Then, when they think they are lost, they realize that they have arrived at the cabin at the lake, a place Paul loved. Later, Cate, Jim, Rory, and Kyle meet up with them, and Cate tells them that the last time they were there, Paul tried c
Cate banishes C.J. and grounds Bridget for going to C.J.'s college keg party. Jim has to take a written drivers exam after being pulled over with an expired license. As Kerry is getting a license too, Grandpa tries to cheat off her, with unexpected results.
Bridget and Kerry are up to something, and Cate is determined to find out what. She discovers that they were planning to send her away for a Mother's Day spa weekend, only to realise they were planning to throw a party while she was gone. Meanwhile, Rory sets up a Car Wash.
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.