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When is an emoticon inappropriate?

EmoticonsThe New York Times ran a lengthy article on emoticons this weekend. It's a must read for anyone who can decipher this symbol ~(_8^(I), or for anyone who can't but would like to.

While the Times gives a brief history of the emoticon, with the first modern usage traced back to 1982, the juicy bits involve the creep of emoticons from casual conversations into the professional arena. For example, if you're writing someone to let them know that a business deal worth thousands or millions of dollars is about to fall through, a frowny face just isn't going to have the same impact as a phone call.

We're betting that a lot of Download Squad readers grew up with emoticons and don't have to turn their head sideways to decipher any but the most complex smileys. But have you noticed yourself wanting to type a quick smiley, wink, or frown into a message to your boss?

Given that sarcasm and other nuances are hard to get across using nothing but text, emoticons offer a sort of shortcut. And when you're typing a note to a friend in a hurry, that's probably OK. But sometimes it's worth taking the long way to say something that's worth saying.

What do you think? Are emoticons the downfall of human civilization as we know it, an evolutionary step in written communication, or something in between?
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