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.

Paul's job as parental guardian becomes more of a full-time position when Cate is up for a promotion and has to spend more time at the hospital. After Paul introduces Rory to baseball card collecting, Rory trades the cards for something not exactly associated with the sport.

The rivalry between Cate and Maggie comes to a boiling point when Maggie gets a sexy, new makeover and gives Bridget a water bra as a gift. Tensions between the Hennessy sisters mount when Kerry and Kyle begin dating, while Bridget's popularity takes a nosedive after she dissed her friends for Donny. Paul becomes concerned when he finds an empty pregnancy test kit.