In the paper the author explores the question ‘Did Wittgenstein (re)invent emoticons?’ in three sub-questions. What did he draw and for which purposes? What are emoticons? Are there similarities and differences between his drawings and emoticons? The answers are following. Wittgenstein has drawn faces from the 1930s to the 1940s which are graphically and by use like emoticons. He presented a philosophical problem of interpretation of faces. Emoticons as made of written and typed punctuation marks or as drawings were invented (...) and used centuries before the 1930s, but common and popular use started in the 1960s. Previous inventions were probably unknown to Wittgenstein, and his faces probably didn’t influence later inventions. His faces and emoticons are graphically similar and made with the similar purposes. Differences are that he only used drawings and never written or typed punctuation marks, and he used them to deal with problems of emotions and perception (similar to his problems of the duck-rabbit head). These answers are connected to available textual and interpretative evidence, interpretations are given in propositions from (a) to (p), and summarized in the conclusion (r). Some consequences of visual thinking on philosophical thinking are also drawn in terms of a future research. (shrink)