Air date: 11/19/02
It's time for summer vacation, but the Hennessys can't decide where to go. Paul wants to go to the cabin at the lake, but everyone else has a nice spot picked out. Rory's idea is Space Camp, Bridget's Mall of America, and Cate's her parents' condo. To settle the issue, Paul initiates a contest. Each family member must give up a bad habit, and the last person standing gets to pick the vacation. Rory, who gives up tattling, is the first to go, then Cate (coffee), and Bridget (telephone), leaving it down to just Paul (the television remote) and Kerry (sarcasm). Paul treats Kerry to dinner at a 50s-style diner, but Kerry remains suspicious. Once they return, Paul admits defeat, meaning Kerry gets to pick the vacation. But the place she picked is the cabin at the lake.
Paul Meets His Match
Air date: 11/26/02
Paul has no idea about how badly he has been treating Bridget and Kerry's boyfriends, until he sees his seemingly friendly new boss, Nick Sharpe, treat Rory in the same manner. This causes Paul to take a change of heart and give his daughters' boyfriends a chance.
All I Want for Christmas
Air date: 12/10/02
It's Christmas time, and Paul hopes to make this Christmas the best Christmas yet. When Paul asks what everyone would like, Rory says he wants a motorcycle, Bridget wants Kyle to spend the holiday with her, and Kerry wants to keep a stray dog she found. When Paul says that Kerry can't keep the dog, she is upset (as usual). Later, Paul writes a column encouraging people to adopt pets, which makes her feel better. Meanwhile, Cate gets the solo part at the Christmas Eve service, and she is nervous that her family will be there. On Christmas Eve, the family helps Kerry with the Pet Adoption Fair at the mall, where every dog, except the one she found, is given a home. Afterwards, they all go to the Christmas Eve service, where they hear Cate sing her solo of "Silent Night" When they get home, she says she is glad they came after all. Paul agrees to let the kids each open a present that night. Rory gets a chemistry set, much to Cate's chargin, Bridget gets the company of Kyle, and Kerry gets to keep the dog she found.
Rory's Got a Girlfriend
Air date: 12/17/02
Rory has a girlfriend named Sabrina Jenkins, and he asks Paul if he can take her on a group date to the movies. Paul allows Rory to go, which outrages Bridget and Kerry because Rory is much younger than they were. Meanwhile, Kerry is upset when Bridget receives a higher test score than her. This leads everyone to think that Bridget is smarter than Kerry. But later on, Kerry receives a letter stating that there was a mistake in the scores and that she actually had the higher score. Not wanting to make Bridget upset, Cate tells Bridget that she got a magazine in the mail.
Air date: 1/7/03
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 - not realizing that the principal is the boring woman in question. Now Kerry is upset because, as her punishment, she must make banners for the pep squad. However, she does think it was kind of cool to have her artwork published.
Kerry's Big Adventure
Air date: 1/21/03
After Kerry and her boyfriend break up, Paul tries to cheer up his blue daughter by getting Bridget to take her little sister with her to a party. But while talking to Kyle at the party, Kerry is shocked when a spark is ignited and the two share a romantic kiss. Paul and Cate try to discover what is hidden in Rory's secret box. They find Paul's sports articles, but Rory really has fireworks.
Come and Knock on Our Door
Air date: 1/28/03
After finding out the she kissed Kyle, Bridget gives Kerry the silent treatment, which is anything but quiet for Paul. That night, Paul has a dream on the set of Three's Company, which parodies the show right down to the last detail. In the dream, Kyle (Jack) pretends to be gay in order to fool Paul (Mr. Roper), so he can have Bridget (Chrissy) and Kerry (Janet). They are soon joined by Cate (Mrs. Roper) and Rory (Larry). Back in real life, Bridget goes to Kyle's new apartment to break up with him.
Drummer Boy – Pt. 1
Air date: 2/4/03
After Bridget is caught sneaking out of the house, she tells Paul and Cate that she has a dream of playing in an all-girl band. Paul suggests she take up an instrument. Bridget chooses to take up drums. Paul hires her a drum instructor, named Ben, who Bridget instantly falls in love with, but is much older than she is. Meanwhile, Kerry is upset with her ex-boyfriend, Jason, when he calls Cate pretty.
Drummer Boy – Pt. 2
Air date: 2/11/03
When Bridget learns that Ben is leaving to go back to his college in Ohio, Bridget decides to follow him. To cover, she says she is going to a sleepover. Kerry invites herself along in hopes of foiling Bridget's plan, but Bridget ends up going to Ohio State University (where Ben goes to college) anyway. Later, Paul and Cate find out and go after them. Rory is reading To Kill a Mockingbird, and wants to find the part where the mockingbird is actually killed (not realizing that there isn't one at all).
Air date: 2/18/03
After a party at Tommy's house is busted by the police, Paul takes the matter into his own hands by volunteering his house for the post-basketball finals party. During the party, Paul falls asleep, and the party gets out of control, as Paul finds all the kids sleeping the next morning. This causes him to lose popularity with the kids' parents, but the kids now find him cool. While Cate is at work the next evening, Kerry and Bridget allow some friends to come over, and it eventually turns into a party, but Bridget and Kerry call it a kid-pack, as it is less than 20 kids. Eventually, Cate comes home and convinces Paul to stop the party/kid-pack, which he does, which causes him to lose all popularity with the kids, and he returns to being the dorky parent the kids found him to be. As a subplot, when Paul tries to help Rory stick up to some bullies at school (though all they'd done was call him one name) at the beginning of the episode, it turns out that he was wearing slippers. He is then on referred to as "Slipper Dad". Rory is also humiliated by this. At the end of the episode, Rory dumps a whole box of slippers on Paul.