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Step 1
Don't use overcomplicated ASCII emoticons. ASCII is the "old school" way of illustrating emotion before the stylized .gif type characters appeared on the scene. Some, like the smiley made by a colon and a paranthetic mark, like this :) are pretty straightforward, but others involving four or more characters can get pretty abstract. Obscure emoticons like <:ox (clown wearing bow-tie??) can be as esoteric as the old ASCII acronyms like ROFL and AFK.
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Step 2
Don't substitute emoticons for words. A message saying simply ":o" is pretty hard to figure out. Sometimes, you can let emoticons speak for themselves, but other times, your reader will be scratching his/her head.
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Step 3
Stick with "stock" characters. Whether you're using ASCII or .gifs, the regular smiley :) and frowny :< emoticons usually convey their messages pretty well (in the right context).
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Step 4
Be discriminate. There are cases where it pays to choose your emoticons carefully. In communications where the outcome is really high-stakes, a ://can be either clear or confusing. When the chips are down, spell out your concerns in letters and words.
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Step 5
Provide a context. Linking an emoticon to the line just before it is the most popular way to let the reader know what the illustration pertains to in a text. Phrases like "What a nice day :)" are clear uses of the smiley. But putting an emoticon out of order or not in context can have unintended consequences.








