:)

I love this, below. First, because I've had the exact same question in my head when composing email to those I figure will take my use of emoticons not as a sign that I am a lousy writer, but that I'm merely having fun. Second, because I love the Chicago Manual of Style's dry-humoured response.

Q. My question is, is there any standard for the usage of emoticons? In particular, is there an accepted practice for the use of emoticons that include an opening or closing parenthesis as the final token within a set of parentheses? Should I (1) incorporate the emoticon into the closing of the parentheses (giving a dual purpose to the closing parenthesis, such as in this case. :-) (2) 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 doubled-chin effect :-)) (3) put a space or two between the emoticon and the closing parenthesis (like this: :-) ) (4) 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 in this note give us added incentive to keep our distance. (But I kind of like that double-chin effect.)

Heh.