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 new kid Damian. Meanwhile, as she waits for the results of her pregnancy test, Cate is stunned when Paul, Bridget, Kerry and Rory seem more concerned about how the baby could disrupt their lives than the blessed event itself.
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.
Donny's parents ask Bridget to be a part of a video message they are sending Donny. They are shocked to discover that Bridget has broken up with their son on the tape. Donny goes AWOL to try and patch things up. Meanwhile, Paul is asked to help give a nickname to a neighborhood prankster who has been terrorizing the block, not realizing that the culprit may be living under his own roof.
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.
Cate persuades Rory to try out for basketball because that would've made his dad proud.
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.
After Cate encourages Bridget to participate in extracurricular activities to beef up her college resume, Bridget shocks the family by landing the lead in the high school production of the story of Anne Frank. Rory's obsession with a dummy named Skeevy becomes a little unnerving for the Hennessy clan.
Cate orders Kerry, Rory, and Jim join the YMCA where Bridget works.
The Hennessy household and Jim are thrown for a loop when Cate's wayward nephew C.J. stops by to pay his respects to Paul and generally keep them company.
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.
After Kerry is promoted to assistant manager at a fast food restaurant in the mall, Jim is hired to handle the register. Meanwhile C.J., who has been employed as a mall cop, busts Bridget for sneaking into a movie without paying, and Cate catches Rory selling worthless family items on the internet under false pretenses.
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.
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.
After witnessing some strange behavior from Bridget and Kerry, Cate tries to find out what they are up to. Meanwhile, C.J. and Rory doubt Jim's ability to put an engine back together after he falls in love with a classic car.
When Bridget is busted over a school dress code violation, Cate is called upon to meet with her new principal. But Cate is in for a shock when she discovers that she went to high school with him. Meanwhile, when C.J. becomes his massage therapist, Jim hurts his feelings when he refuses to admit that his grandson has become good at something.
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.