There are at least three types of situations in which this can happen to an average person.
The first type of situation is one in which we are exposed to jargon, or to the technical use of a term, for the first time. For example, this happened to me when I first studied Constitutional law. I had heard the word “taking,” of course, but I had never heard it used as a noun to refer to an area of law regarding government regulation and how much it detracts from the value of someone’s property.
A second type of situation is one in which someone sees the world differently than we do and therefore uses words in ways that we would not. An example of this for me is Emile Durkheim’s use of the word “organic” to describe modern society. When I hear the term “organic solidarity” it makes me think that all the people in the society are essentially the same because they are part of one organism. But Durkheim uses it in just the opposite way. He says a society is “organic” when the people have less in common because he sees an organism as something where the various parts are different and therefore need one another.
A final type is when a word is coming to be used in a colloquial way and we are not familiar with that usage. An example of this would have been when one of my students first used the word “chronic” to refer to marijuana.
All of these are situations in which I have heard familiar words used in ways that confused me.