Should you start an e-mail with “dear” or “hey”? What’s the proper
punctuation for emoticons? Did reading this headline make you cringe? In
the digital age, does proper spelling and grammar even exist? Stephen Strauss on the trouble — and potential benefit — of literary shortcuts.

Recently on a freelancers’ internet discussion group I asked for the name of an editor at a certain magazine who I could pitch an article idea to. Names came back as did the following response: “I hate to be pedantic, but it’s whom does one pitch to.”

To which I replied “While I stand corrected, it has been my experience that people who say they hate to be pedantic, actually like to. Or maybe that should be like to whom. :)”

Which led to something I couldn’t have predicted. We soon were involved in an animated discussion concerning the correct punctuation for the emoticon I used. Is the right presentation “to whom :)?” or “to whom? :)” or something different if you moved from a 🙂 to a 😉 not to mention to a “)? And when nobody was quite sure, the debate shifted to a larger discussion of the role of emoticons in writing. Were they the alps of literary juvenilia, the kind of affectation which you might use among friends but in the larger writerly world were the sign of a dumb-dumb brain? One argument which arose was that a true stylist should be able to write in a fashion that told readers they were joking.

And this split off into another discussion of what was proper spelling/grammar in an internet age. If you wrote “r” for “are” and “u” for “you”, did that say you were infected with bacillus nincompoopness? And what about salutatorians and valedictions in a tweet/text/blog/email context? When did you start a missive with “dear” and when with “hi” or “hey”, not to mention when with nothing at all?

All of which now leads me to a simple proposition. I can’t speak about the state of literary elegance or aptness in the 21st century, but I will suggest that today may be the most interesting period in grammar and standards usage since the arrival of the printing press. Effectively the “who” and “whom” debate doesn’t make any difference. But discussions of what is useful and proper in an age in which new technology has increased the amount we write  while decreasing the amount of time we spend composing it.

In this light, for example, the emoticon is actually a new kind of punctuation mark which really is useful in telling people the emotional tone of words we dash off.  And when we don’t use them, misconceptions can and will abound. For example I will suggest that the recent furor over Tom Flanagan’s emailed response to a woman who criticized his suggestion that a hit be put out on Julian Assange — “Better be careful, we know where you live” were Flanagan’s exact words — was in fact caused by his leaving a necessary emoticon out.

And the reality is that the increased amount of time we spend writing means most people are never going to make their email words more precise by using traditional punctuation.

The same is true with spelling and “r’s” and “u’s”. They allow us to move on to the next correspondence quickly, important in a world of Blackberrys and the like. And we are never going to have more time to say the same thing with the longer spelling. In 2010 it appears medium is not just the message — it is the grammar and the spelling and the punctuation of the message too.

Having said that, what I would like is for someone to establish some conventions. There may well be principles where something that is useful in one context looks sloppily offensive in another. I say this because, personally, I am tired of having to ask myself if this emoticon is appropriate for this email. Or if this person I am writing to should be addressed as “dear” instead of “hi”. The truth is that I can’t tell, because nobody knows. Things are still so new nobody has agreed upon what is proper. Proper in the sense of effective. Proper in the sense of recognizing internet communication is different. Proper in the sense of knowing change is necessary.

And that’s what I want. I want standards that make sense and that I can refer to without thinking. Because it seems to me that standards will let us communicate with less grammatical uncertainty and better communication will make everyone :)er.