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Further Reading
Talking with Eliza
Turing's Child Machine
Skinner's Behaviorism
Strong or Weak?
Ambiguous Words
Ambiguous Words
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Why do computers have such a hard time at understanding natural language? Wouldn't it be fair to expect that given the rules of grammar and the definitions of all words in a language, computers would be able to find their way around?

The answer, to put it shortly, is no. And the reason for this blunt response has to do with the innate complexity, vagueness and subtlety of human language.
For humans, language is a powerful and endlessly reshapeable tool. Our ability to build infinite worlds out of a finite number of words is derived from the fact that there are more meanings in a language than there are words. This vagueness begins at the level of the basic unit of language - the word. Most words, in and of themselves, are ambiguous. The word "plane", for example, can mean either a flat or level surface, or an airplane. We derive the meaning of the word from its connotation - from the other words which surround it. The sentence "I took the plane there", can hardly be misconstrued to mean that the person speaking hauled a flat surface to his destination. But how can a machine differentiate between the two meanings and make sense of this sentence? By what rule can it make the obvious choice?
On the same account, but with a slightly higher degree of complexity, are figures of speech. When we say "I ran into my friend", no person would think that we actually crashed into that friend at top speed. It would be immediately understood that we are speaking about a meeting, that for all practical purposes could have even happened sitting down. But a computer stands a much smaller chance at interpreting this vagueness.
Ambiguity is a characteristic of language
The ambiguity of the human language did not have to wait for the accelerating research into artificial intelligence in order to present itself as one of the basic characteristic of speech. It is at the roots of the spoken and written word, and is abound in every form of literature and poetry, as ancient as the ancient Greek writings. The modern day science of semantics deals with the ambiguity of language and classifies its instances into groups such as anaphora, metonymies and synecdoche.