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.

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.

After Kerry and her boyfriend break up, Paul tries to cheer her up by getting Bridget to take her little sister with her to a party. Meanwhile, Paul and Cate try to discover what is hidden in Rory's secret box.

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.

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 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, 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. 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.

Kerry gets in the art program in Europe in the summer, but Cate forgot to submit her medical records in time. Together they appeal to principal Gibb. C.J. falls for Missy's big sister Sissy and Gramps for a woman he has a car accident with.

Kerry is livid when Bridget unintentionally makes a mockery out of her art project at the mall. But she forgets about Bridget when a fellow artist asks her out on a date. While C.J. finds himself striking out at speed dating, Jim discovers that he's a hit with the ladies.