I think some of the misunderstanding comes from projecting in to the words used. For instance, "a successful date" can mean many things, like "not a crazy person", "good company, good time", "nice chemistry, we'll see each other again" etc. And it also can mean "score!" or "cosmic twin soul!". Without precise contextualization, the brain has a tendency to fill in the gaps, and often it misses the mark.
As for generalizations, the other day a friend's wife was complaining about the new generation of student she's having: they're arrogant, entitled, etc.. Of course there are kids who do not fit that description, but within the flow of a conversation, there isn't always the need to explicitly interrupt with the caveat that this generalization doesn't apply to every single individual if it is implicitly understood.
As for generalizations, the other day a friend's wife was complaining about the new generation of student she's having: they're arrogant, entitled, etc.. Of course there are kids who do not fit that description, but within the flow of a conversation, there isn't always the need to explicitly interrupt with the caveat that this generalization doesn't apply to every single individual if it is implicitly understood.