Paul is left home alone with the kids while Cate is at a seminar on the day of the big Michigan/Ohio State football game. But much to Paul's dismay, the game soon takes a backseat when Bridget is accused of shoplifting and Kerry gets upset over her latest cause.

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.

Bridget takes drastic measures when an overprotective Paul keeps coming up with excuses to delay her from taking her driver's test. Meanwhile, after convincing a less-than-confident Kerry that she has the talent to enter an art competition, Paul is shocked and Kerry is devastated when her submission is rejected.

A sports-struck Paul lets Bridget do whatever she wants when she breaks up with Kyle and begins dating high school basketball wonder Travis "The Rainman" Smith – whose father just happens to be Michigan baseball legend Steve "Canned Heat" Smith (Terry Bradshaw). Meanwhile Kerry resents the fact that Paul still thinks of her as a little girl and not as a budding teenager ready to take on the dating world.

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.

In an effort to win back the love and respect that his daughters used to show him when they were young, Paul turns to a parenting book for some quick advice. But when Bridget and Kerry discover Paul's teaching tool, they try to use it to their advantage to get their father to let them go to a rock festival.

Paul's plan backfires when—after telling Bridget to tell Kyle the truth about her date with another boy—Kyle breaks up with her. Meanwhile, Kerry's first date turns out to be a dream, but she is devastated when the boy doesn't call her back.

When no one can agree on where the family vacation should take place, Paul challenges the Hennessey clan to give up their bad habits for a week – and the winner gets to choose the vacation spot. But the family's vices soon get the better of them, and secret collaborations and clandestine alliances threaten to foil the contest.