This wonderful bit is from Harper's Magazine, February 2007.

[Prescriptions] STET OFFENSIVE

From questions posted on the website of The Chicago Manual of Style, answered by the University of Chicago Press manuscript-editing department.

Q: Is there any standard for the usage of emoticons? In particular, is there an accepted practice for the use of emoticons that includes an opening or closing parenthesis as the final token within a set of parentheses? Should I incorporate the emoticon into the closing of the parentheses (giving a dual purpose to the closing parenthesis, such as in this case :-); simply leave the emoticon up against the closing parenthesis, ignoring the bizarre visual effect of the doubled closing parenthesis (as I am doing here, producing a double-chin effect :-)); or avoid the situation by using a different emoticon (some emoticons are similar :-D), placing the emoticon elsewhere, or doing without it (i.e., reword to avoid awkwardness)?

A: 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 is in this note give us added incentive to keep our distance.

Q: Is there an acceptable way to form the possessive of words such as Macy’s and Sotheby’s? Sometimes rewording to avoid the possessive results in less felicitous writing.

A. Less felicitous than “Sotheby’s’s”? I don’t think so.