It turns out that the emoticon might be a bit older than we originally thought. Literary critic Levi Stahl has found what could possibly be the first instance of a 🙂 in Robert Herricks 1648 poem To Fortune. Stahl checked to see if it was just a typo in the edition of Hesperides that he owns, and says that he found the smiley intact in the authoritative two-volume edition of Herricks work published last year by the Oxford University Press.