After Paul convinces 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.

After discovering that boyfriend Kyle kissed Kerry at a party, Bridget gives her sister the silent treatment which is anything but quiet for Paul. But real life merges with fantasy when Paul has a dream that lands him in familiar territory, showing Kyle as a swinging bachelor living with Paul's two beautiful daughters in an apartment straight out of the 70s.

While vacationing in Florida at Cate's parents' home, Paul and Cate catch Bridget and Kerry on the news partying with a group of Spring Breakers. But the news runs archival footage that features a young Cate letting loose in a bar. Meanwhile, a jealous Paul meets Cate's college boyfriend Byron and Rory befriends an elderly gentleman whose stories about World War II turn out to be more fiction than fact.

Rory steals a police dog when he hears about CJ's glory days of stealing his old school mascot, but Cate is shocked when the dog finds marijuana in Kerry's backpack. Meanwhile, Bridget gets brought home by the police for not wearing a helmet on her boyfriend's motorcycle after Cate telling her she has to.

After being told that she's fickle when it comes to relationships, Bridget is afraid that she may end up hurting Jeremy's feelings when her ex-boyfriend returns to town. Meanwhile, Kerry is outraged and plans revenge when provocative dancing has been banned from the high school formal, which is being chaperoned by Cate and Jim. C.J. partners with Rory to broadcast school scandals over the internet.