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 Damian - a sexy new kid at school. 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. In fact, the only support Cate seems to be getting is from her nosy neighbors, the Doyles, who share a well-kept secret about their own family.

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.

When Fred and Mary Ellen Doyle ask Bridget to be a part of a video message they are sending to Donny at the Naval Academy, they are shocked to discover that Bridget has broken up with their son on the tape - and 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.

The Hennessy famly must deal in their own way with the unexpected death of Paul. Cate's separated parents, Jim and Laura, come to visit and try to console the grieving family.

The family finds Paul's last written article, and reads it just before going to sleep.

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 when he learns that they are planning to attend a party with their boyfriends on the holiday. Meanwhile, Laura's visit to the Hennessy household ignites sparks between her and Jim.

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. But after reading Anne Frank's diary, she doubts her own ability to play the role. Meanwhile, Rory's obsession with a dummy named Skeevy becomes a little unnerving for the Hennessy clan.

Cate decides the family isn't active enough and takes them to join the YMCA where Bridget works. Jim is overprotective of her at the YMCA and doesn't think she should be working there. Meanwhile Rory deals with a coming-of-age issue that keeps ""popping up"" at the worst of times.

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. But the irresponsible C.J. can't seem to resist getting himself into trouble when he advices Rory on techniques about kissing a girl and takes the blame when Kerry - driving with a learner's permit -- accidentally dents Cate's car driving Bridget on a late-night errand.

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. 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 need of a tutor to boost her grades, Bridget hires Jeremy, hoping to make her chance of getting into a good college better. However, after her boyfriend gets sick, Bridget tries to persuade Jeremy to take his place. 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, which ends up just being Tylenol.

Bridget decides to make a move on her brainy tutor, Jeremy, 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 his now homeless nephew.

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, a member of the high school's PTA committee.

On the advice of the family therapist, Cate is encouraged to pursue a once-thought-unobtainable 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 -- and 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. But when she witnesses his disdain for the customers, Kerry is faced with the dilemma of having to fire her grandfather. 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 - Paul's successor at the newspaper - 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. But after meeting up with C.J., the girls find themselves at a familiar location that was beloved by Paul. 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 -- not suspecting that they might be trying to set up a special Mother's Day getaway for her. Meanwhile, C.J. and Rory doubt Jim's ability to put an engine back together after he falls in love with a classic car -- which is in for a wax job at Rory's new detailing service -- and decides to fix a noise in the motor

When Bridget is busted over a school dress code violation, Cate is called upon to meet with her new principal, Ed Gibb. But Cate is in for a shock when she discovers that she went to high school with Ed -- who remembers it vividly -- though she doesn't remember him at all. Meanwhile, when C.J. becomes his massage therapist, Jim hurts his feelings when he refuses to admit that his wayward grandson has become good at something.

Part 1 of 2. Cate finds herself once again in the awkward position of having to deal with Principal Gibb when she forgets to turn in a health form for Kerry's trip to Europe. Meanwhile, Cate is resentful of Jim's relationship with Tina because she still hopes that her father will reconcile with her mother, and Rory plays a nefarious joke on C.J. when he sets him up with girlfriend Missy's already engaged sister, Sissy.

Part 2 of 2. When Cate discovers that Bridget took the fall for Kerry for organizing the school sit-in, she agrees to have coffee with Principal Gibb in order to set the record straight. But the girls are convinced that their mother's innocent coffee meeting with their principal is really a date. Meanwhile, Kerry is furious when Bridget is elected student body president and wins a trip to Washington, D.C. -- because everyone thinks she organized the school sit-in -- C.J. keeps deluding himself that he's been chosen to be a roadie for Aerosmith over the summer, and Jim agrees to let Rory travel with him to Florida -- where he plans to try and win back his wife's affections.