As Cate decides to go back to work as a nurse, Paul undertakes the responsibility of watching the kids.

After seeing how much money Bridget spends on keeping up with the latest fashions, Paul tells her to go out and get a job to learn how to be fiscally responsible. But when she lands a job at a trendy mall clothing store that offers its workers a 40% discount, Paul and Cate begin to worry that she may not be learning the true value of a dollar.

A sports-struck Paul lets Bridget do whatever she wants when she starts dating Travis, star basketball player and son of baseball legend Steve Smith. Meanwhile Kerry resents the fact that Paul still thinks of her as a little girl.

Bridget is ecstatic when the cheerleading squad has an opening for a new member. But after telling Kerry that she is not cut out to be a cheerleader, Bridget is completely dumbfounded when her sister tries out and is chosen for the team. Meanwhile, Paul tries in vain to wean Rory off video games and introduce him to the world of books.

Paul seems to be the only one looking forward to a family Halloween, as Bridget, Kerry and Rory make plans to spend the spooky evening away from home and with their friends. But Paul's wish to relive the past by having the family get together for one last Halloween campout in the old treehouse may turn out to be the biggest nightmare of the evening.

When a proud Paul lets thirteen-year-old Rory go out on his first date, Bridget and Kerry accuse him of unfairly changing the rules because they were never allowed to date at that age. Kerry is shocked when Bridget receives a higher score then she did on a state aptitude test.

After a party at Tommy's house is broken up by the police, Paul chastises his friend and unwittingly volunteers to host the next one. But when the party gets out of control too, the kids think of him as a cool parent, while the neighborhood parents think he's just as unreliable as Tommy.

Bridget and Paul are surprised to find themselves in similar situations when they are both alienated in their social circles. But they devise a plan to settle the score, leading Paul to crash a poker game with Tommy to get closer to boss Nick, and Bridget trying to break up ex-boyfriend Kyle and her nemesis Jenna.

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.

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 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.