Sadface
Q. I’ve been messaging with a guy I recently met, and lately I’ve been wondering if it’s okay to use smiley faces in flirtatious emails. Sometimes I use it to milk the “I’m a cute girl” factor, but is it still okay to do that?
A. If you’re familiar with my thoughts on w00t, you can probably already predict that my answer is an emphatic “No.*” Leave the smiley faces to the reigning teen prom queens of the world. English has (hyperbolically speaking) the most words of any language. Certainly there are ways to get your coquettish point across without succumbing to emoticons and the like.
*The only exception I will allow is if the two of you get into a discussion of the various stages in Prince’s career. In such cases, the 
or O(+> may be used to demarcate his pre and post “Artist Formerly Known As” era.
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