Caroline in the City is an American situation comedy that ran on the NBC television network. It stars Lea Thompson as cartoonist Caroline Duffy, who lives in Manhattan in New York City. The series premiered on September 21, 1995 in the “Must See TV” Thursday night block after Seinfeld. The show ran for 97 episodes over four seasons, before it was cancelled; its final episode was broadcast on April 26, 1999.

The film is a romantic comedy about a Portuguese widow whose husband had been a fisherman who died at sea. The widow’s teenage daughter wants to be a professional gambler and she convinces her mother to date a British man whose new in town. The widow falls for the Brit, who pretends to be in the fishing business but is actually a professional gambler. The naive daughter gets into some trouble.

Because of his salacious language, late-night radio advice-show host Leon Phelps, along with his sweet and loyal producer Julie, is fired from his Chicago gig. Leon gets a letter from a former lover promising a life of wealth, but he doesn’t know who she is. Can Leon find his secret sugar-mama? What about Julie?