Sydney Shep, a New Zealand scholar, has found evidence of typeset emoticons in nineteenth century typesetting. Interesting.
However the nineteenth century is not the fourteenth. Shep argues that some of the annotations in medieaval manuscripts are the precursors to emoticons. Other scholars argue differently.
Whatever the truth, it's interesting how different cultures deal with texts and structure them. For me the question is, do you see similar scribbles in greek and roman manuscripts, be they highlighting or be they the analogs of emoticons, to add metadata to text?