How does the term "speakeasy" illustrate generational differences in the story?

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Without knowing the specific story to which you are referring, this answer will need to be somewhat general. However, the term "speakeasy" indicates the probable connection of one of your two generations with the time period of the Prohibition Era (roughly 1920-1933) in the United States.

A speakeasy was a business that sold alcohol (probably along with legal beverages and food) at the time when sales of alcoholic beverages was illegal. As a result of this illegality, the speakeasy did not advertise all of the products it was selling.

In today's culture, an establishment that sell illegal drugs as a sideline could be termed a speakeasy by someone from a previous generation who recognizes the similarities in business practices.

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