How to Know When to Use Emoticons. Words can sound harsh when delivered without a wink or a smile to let other Internet users know you meant your point was friendly or humorous. Sometimes, though, you can use emoticons inappropriately. Here's how to know when to employ them.
Consider the context. If you're in a chat room, instant-messaging, posting on a discussion board or writing an informal email, an emoticon can lighten the mood and convey your point. Even with some work emails, a simple smile can make a request to another employee seem less harsh. Emoticons are not appropriate in job application cover letters, emails to superiors or officers of your company, complaints to a government official or in any other context in which you need to be taken seriously.
Check how many emoticons you've already used in your email or discussion post. An excess of emoticons might make you seem immature. Teens and tweens often use them excessively. One per form of correspondence is plenty for adults.
Keep your emoticon simple. The basic smiley, angry face, wink, sad face or laughing face are all you need. Getting fancy with animated punching smileys or figures that represent Sadaam Hussein or Homer Simpson will seem silly to most grown ups, especially in work emails.
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Let your words do most of the talking. In person, our facial expressions and gestures do some of the work of communication but what we say tells most of the story. Online communication is similar. A smiley or wink might suggest your words should be taken in a friendly context, but your words matter the most.