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Papers and prescriptivists, style and smileys

Louis Menand evokes the hell of undergraduate term paper end notes, skewers the evil that is Word, and takes the Chicago Manual of Style to task in a recent New Yorker piece on end matter. Sucker for the Borgesian that I am, I like his summary of the perfect prescriptivist view:

The Manual is not too long. It is not long enough. It will never be long enough. The perfect manual of style would be like the perfect map of the world: exactly coterminous with its subject, containing a rule for every word of every sentence. We would need an extra universe to accommodate it. It would be worth it.

Prior to that he chides the Manual for encouraging excessive politeness:

Some of the advice is frankly a matter of taste. "An exclamation point added in brackets to quoted material to indicate editorial protest or amusement is strongly discouraged, since it appears contemptuous," the authors counsel. "The Latin expression sic (thus) is preferred." First of all, the reason the bracketed exclamation point appears contemptuous is that you use it when you wish to express contempt. There is nothing wrong with contempt. Second (which Chicago insists on, although generations of pedants have believed "secondly" to be the proper usage), sic is a far more damning interpolation, combining ordinary, garden-variety contempt with pedantic condescension.

As for me, I'm guilty of the inconsistency and relativism he damns in the Manual as well as of some specific sins both he and Chicago condemn. For instance, I have the programmer's preference for putting punctuation inside quotation marks only if it logically belongs there, 19th-century schoolmarms be damned. That is,

He mumbled the mild oaths "gosh", "darn", and "golly" in turn, then shouted "dammit!" and left the room.

I was discussing this with non-programmer Christina the other day, who is no doubt shouting "[!]", "sic" and worse as she reads this, thinking my 21st-century opinion on this matter to be an affront to good taste. So I asked her the punctuation question that's been bugging me ever since I started writing online.

When a smiley terminates a parenthesis, do you use an extra right-paren or do you let the smiley itself do the job? And if you use two, do you put a space between them? E.g.,

(How now brown cow. :-)
 
(How now brown cow. :-))
 
(How now brown cow. :-) )

The middle choice seems most logical but I don't like the implication that I have a double chin. So far neither the style manuals nor the freelance mavens have settled this one.

books 2003.10.18 link