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.