Examples given in this paper deal with print media, but the argument applies to all media. These examples illustrate structural-linguistic principles, principles that may be extended to any medium. The approach is structuralist.The history of handwritten and printed texts in the West is an inseparable history of punctuation and lettering. Written and printed texts represent spoken language: letters are representations of segmental-phonemes (linguistically meaningful sounds); graphemic punctuation represents meaningful supra-segmental phonemes (intonation, pitch, pause, etc.).Alphabetical, graphemic representation in the West has through the ages developed many arbitrary systems of grammatic punctuation to show speech, but the semantics of speech representation remains under-developed. This is no less true of digital media as of print media. Digital print media are particularly vulnerable to ambiguity. Emoticons and emojis came about of necessity. Just as early-print punctuation was primarily invented by printers and printers’ devils, not scholars, so too emoticons are Silicon-Valley formalization of user-invented semantic punctuation. :-) becomes [smiley emoji] or [smiling alien emoji]. :-( becomes [frowning emoji] or [frowning alien emoji], and so on—and ambiguity is the hothouse of error and misreading that affects all media. We should not be surprised. It is said that a similar devil, Titivillus, caused medieval manuscript scribes to make errors in their copying.I am specifically interested in the ramifications of semantic punctuation on philosophical texts—above all, irony, though sarcasm, ridicule, double entendre, derision, mockery, satire, scorn, sneering, scoffing, gibing, taunting, acerbity, causticity, hate, trenchancy, etc., as well as positive expressions such as love, amusement, friendliness, approval, sincerity, etc. are also of semantic-punctuation representational importance. Does the failure of traditional written and printed tests to reflect, for the most part, semantic values handicap printed representational discourse? In fact, can the handicapped discussion of profound ideas be adequately represented graphemically and philosophical inquiry limited without representation of the full range of human linguistic communication?Representation of irony in print has long escaped writers and scholars. In the 17th century, John Wilkins in An Essay towards a Real Character and a Philosophical Language (1668) proposed, among other semantic punctuations, an inverted exclamation mark (¡) to indicate irony: “That is terrific work¡” for a job poorly done. “What a lovely hat you have¡” said with sarcastic irony to someone sporting a ridiculous hat. (Later, an inverted question mark was suggested for ironic statement, ¿, but confusion with Spanish inverted question marks makes it a less attractive alternative).Wilkins’ term “philosophical language” refers to language as printed representation, not speech. His argument is an early reference to what I have elsewhere argued is the failure of “bookish philosophy” that has come to typify academic philosophy, for example, the gibberish of Heidegger, Derrida, post-structuralists, post-modernists, post-humanists, numerous analytic and “linguistic” philosophers, and many others.One possible way out of these difficulties is a process of mediation, unmediation, and immediation.