Coudal linked to this interesting article on Art Lebedev about some common problems with typesetting punctuation, such as centering, tracking and bolding. I agree wholeheartedly with all of them, though I’m interested at the solution to the problem of how to punctuate smileys. I may be an old traditionalist here, but I think if you’ve got smileys in your text, you’re not going to be typesetting it. If you have to then you may as well set the smiley in Wingdings and treat it as a normal glyph, rather than leave it as two punctuation marks. Still, when typing in plain text and you’re prone to using smileys, here’s an idea of how to use punctuation with them.
Notice on the Art Lebedev site that the paragraphs are numbered? That’s interesting, no?