Augustine is most probably unique among the classic philosophers in the Western tradition by beginning to examine this question by observing babies.
By watching babies he determined that they are always in a world of flawed interpretation. Before they learn language, babies make signs in an attempt to convey meaning, but this is not perfectly understood by older persons watching them. The baby becomes frustrated and begins to cry.
Once children acquire the power of speech, Augustine says they enter the "stormy life of human society" where we are forever trying to signify meaning and finding that communication is always flawed.
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