Modern Emoticons in Legacy Punctuation

emoticon - winking smileI like emoticons. That’s no secret. I think at least the basic ones add useful clarity to communication as well as a little welcome whimsy* **. The problem here lies not with emoticon haters, but punctuation.

Let’s say I write something like, “The Sun loves being sexy,” and then in parentheses I add, “That’s hot” with a trailing smiley emoticon “:-)” There are three formatting choices:

  1. The Sun loves being sexy. (That’s hot :-)
  2. The Sun loves being sexy. (That’s hot :-))
  3. The Sun loves being sexy. (That’s hot :-) )

The basic problem is one of balance. We all know that opening and closing parentheses need to be matched. Doing otherwise can only lead to anarchy, dogs sleeping with cats, and possibly hemorrhoids. (1) isn’t balanced since the closing paren in the string isn’t matched with the left, it’s actually part of the symbol. (2) has balanced parens, but it also suggests that the usual trigraph smiley is a different tetragraph smiley, i.e. a smiley with a double chin. (3) Is very similar to (2), and could be interpreted similarly, but adds enough separation for clarity.

The third option is also my favorite because the solution applies to another similar problem: URLs that abut punctuation in sentences. This happens a lot. Let’s say you want to link to in your text. In this case, surrounded by spaces, it’s not a problem. But if there’s a comma or period (or heaven forfend, a slash) then you are introducing an element into the URL that likely invalidates it. E.g.

  1. I think is great.
  2. Go to, it’s great.
  3. Go to , it’s great.
  4. A great place is
  5. A great place is .

As mentioned, (1) isn’t a problem; (2) & (4) often cause issues or inconvenience; and (3) & (5) solve the issue with a clarifying space. The problem with (3) & (5), of course, is that it offends the sensibilities of many a punctuphile and not a few style guides, but screw them — this is more accurate and functional***.

Since there is no department/ministry of English mandating these things, it’s up to the hoi polloi to sort out the accepted conventions (rules are few and frequently excepted, anyway). I figure I’m as polloi as the next person, so I get an equal say. I say: add the clarifying space.

Oh…and also a nod to xkcd, since just about everything has an applicable xkcd at this point.

* I’m speaking about western emoticons. Eastern, 2channel, and emoji have their own issues.
** Restraint must be shown, of course, because emoticons can get very long and obtuse.
*** Don’t get me started with American quotation marks.

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