I’m glad that Randall has the guts to tackle the tough issues facing the world today: emoticons in parenthesis. Check out the comic.

Since I’m starting my own copyediting and proofreading business, this issue is particularly timely and relevant for me.

Randall outlines the basic options:

• blah (or blah :)
• blah (or blah :) )

The first option looks like the author threw an extra colon in there.  The second option looks like the author mashed the keyboard with her elbow.

We also need to consider these options:

• blah (or blah :-)
• blah (or blah :-) )
• blah (or blah :-D)
• blah (or blah :-D )
• blah (or blah :-)-)
• and what about (this (or this (it gets ridiculous fast :) ) )

“American” English writing style is primarily dictated by two style guides: The Chicago Manual of Style (CMOS) and The AP Stylebook.

I could only find references to emoticons and parenthesis in CMOS, and it dodges the question (source):

Until academic standards decline enough to accommodate the use of emoticons, I’m afraid CMOS is unlikely to treat their styling, since the manual is aimed primarily at scholarly publications. And the problems you’ve posed in this note give us added incentive to keep our distance.

If the experts are no help, what are we to do?

Thankfully the web makes everyone a Certified Internet Expert (including me :) ), so follow along as I puzzle it out.

Round One

• As a programmer I want each open parenthesis “(” to match exactly one close parenthesis “)”.
• As a writer I realize that an emoticon must be considered as a whole, not merely as a collection of individual characters.  Therefore any parenthesis or other character within an emoticon should have no bearing on the punctuation of other words.

Round Two

• As a programmer I know that I will try to visually match each parenthesis pair I see.
• As a writer I find “) )” slightly less offensive than “))”.

Round Three

• As a programmer I will use sed or vim or a Firefox hack to rewrite any text I don’t like, so I don’t really care what you writers think.
• As a writer I want the rules that govern “:)” to match the rules that govern “:D”.

The Decision

As a Certified Internet Expert I decree that emoticons shall be considered as a single symbol.  An emoticon shall always be followed by a space.  If an emoticon ends a parenthetical phrase, the closing parenthesis that matches the opening parenthesis must be used, regardless of whether the emoticon itself contains a parenthesis.

Correct examples:

• He said he would be happy to do it (he lied :) ).
• He lied (she knew he would :D ).

Tune in next time for another exciting episode of geeky grammar.