I used to work in a related field (hence being at conferences etc). Issues I recall are:
Some (human) languages have grammars that are purely positional. In those it is much easier to deduce what is the object and what is the subject. English is not one of those languages. This is why it's so easy to make alice produce gibberish.
There are a lot of people working on "context free grammars", particularly those working on the so-called "semantic web". If you can map human language to a CFG then it's much easier to deduce appropriate responses, and to elicit definitions of new terms (like yuloaifs) in interesting ways.
There is a base vocabulary of around 200 words that should be enough to establish the grammatical basis of an expression.
Human language is inherently fractal, in that each clause and sub-clause can be expanded into a phrase that defines it. The problem is that these in turn can be expanded. For example, "water ski" -> (liquid state of H2O) (horizontal slat that is placed on sole of foot for sliding over low friction surfaces) OR (act of sliding over a low friction surface, that being) (liquid state of H2O) -> ((fluid that is not a gas) (energy dependent phase of matter) (substance: H2O) ) ((plane perpendicular to the direction of gravitational field)( thin section of solid substance in form of rectangular prism) (verb: suppositional) (base surface of) (extremity of lower limb) (preposition: purpose of) (moving tangentially with minimal friction) (qualitative comparison: low) (heat producing force opposing direction of motion)) -> etc.
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