I hate to be a party pooper — no, really: I hate it — but I just don’t think Levi Stahl has found an emoticon in a seventeenth-century poem — nor, for that matter, that Jennifer 8. Lee found one from 1862.
About Stahl and Robert Herrick. If we were really serious about finding out whether Robert Herrick had used an emoticon, we’d look for his manuscripts — since we could never be sure that his printers had carried out his wishes accurately, especially in those days of highly variable printing practices. But those manuscripts, I think, are not available.
The next step would be to look online for a facsimile of the first, or at least a very early, edition, and while Google Books has just such a thing, it is not searchable. So, being the lazy guy that I am, I looked for nineteenth-century editions, and in the one I came across, there are no parentheses and hence no emoticon:
So it’s possible, I’d say likely, that the parenthesis in the poem was inserted by a modern editor. Not that parentheses weren’t used in verse in Herrick’s time — they were — but not as widely as we use them today and not in the same situations. Punctuation in general was unsettled in the seventeenth century — as unsettled as spelling: Shakespeare spelled his own name several different ways — and there were no generally accepted rules. Herrick was unlikely to have had consistent punctuational practices himself, and even if he did he couldn’t expect either his printers or his readers to share them.
So more generally, I think Stahl’s guess is ahistorical. The first emoticons seem to have been invented about thirty years ago, and are clearly the artifact of the computer age, or, more specifically, a purely digital or screen-based typewriting-only environment — because if you were printing something out before sending it, you could just grab a pen and draw a perfectly legible, friendly, not-rotated-90-degrees smiley, or frowney, or whatever, as people still do. Emoticons arose to address a problem that did not and does not exist in a paper-centric world.
And one final note: in the age between the invention of the typewriter and the transition to digital text, people certainly realized that type could make images — but they were rather more ambitious about it.