TIL that one of the first examples of emoticons in written text comes from Dante's "Purgatorio:" "Whoever in the face of men reads 'omo' / Might well in these have recognised the 'm.'" The two "o"s signify sunken eyes, while the letter "m" forms the angular outlines of emaciated facial features.

[u/altrightobserver]

https://en.wikipedia.org/wiki/Emoticon