Everything is older than you think it is:
We interrupt our blogging of Daniel Deronda to share breaking news: In reading some of Robert Herrick’s poetry last night, I discovered what looks to be the first emoticon! It appears at the end of the second line of “To Fortune,” which was published in Hesperides in 1648
Here’s a scan of the original printing:
Only, no, probably not. As Ben Zimmer at Slate points out, punctuation inside parentheses was fairly common in the 17th century, and there are numerous examples of colons appearing just before a parenthetical close.
So, entertaining as it might be, it seems that Herrick didn’t use the first emoticon.