“If you choose an answer at random, what is your probability of being correct?” The question is, I think, pragmatically ambiguous. It features neither lexical nor structural ambiguity, yet the joke hinges on understanding the question in more than one way.
Recently I have been re-reading James Thurber’s “Ladies’ and Gentlemen’s Guide to English Usage”, a parody of Henry Watson Fowler’s Dictionary of Modern English Usage. The parody is built around a central conceit: that a language usage guide is equivalent to lifestyle or relationship advice. This is not merely a conceit around which to build a parody; it is also a fair assessment of what usage guides are used for.
A light-hearted dialogue on the meaning of “free will”, inspired by Karl Smith at Modeled Behavior.
Nice interview with Arika Okrent on her new book “In the Land of Invented Languages” including a good description of the Whorf Hypothesis and an in depth discussion of a variety of invented languages.