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How do you treat an emoticon at the end of a sentence?

He probably caught his cold from the kids at school :(

Should there be a period after the :(, or should I go straight into the next sentence (capitalizing the next word)?

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Nice question :). I often debate putting a '.' after a smiley. I'm tempted to, but it doesn't look good IMHO. –  asymptotically Sep 8 '12 at 1:43
    
... or even before the smiley. –  w3d Sep 16 '12 at 18:13
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2 Answers

Emoticons are not used in formal writing, so how they are punctuated is really just a matter of style choice. It depends on how you conceive of the function of emoticons.

We can think of emoticons as a parenthetical expression of emotion that helps the reader to understand the text (e.g., "(I feel sad.)"). In this sense, they are rather like stage directions in the script for a play.

Since emoticons are extraneous to the meaning of the sentence and can stand on their own, I would suggest only punctuating the sentence proper.

He probably caught his cold from the kids at school. :( I hope he feels better tomorrow.

This would be roughly the equivalent of

He probably caught his cold from the kids at school. (I feel sad.) I hope he feels better tomorrow.

If instead you feel that an emoticon instead represents terminal punctuation (e.g., a sad exclamation point), as some commenters have suggested, then you would leave off the period altogether since further punctuation is not necessary.

He probably caught his cold from the kids at school :( I hope he feels better tomorrow.

In any case, I think it would be improper to put a period after the emoticon.

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I'd add that since emoticons are a pretty new concept -- or quite possibly a passing fad -- rules for their usage are far from established. –  Jay Sep 7 '12 at 17:51
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I disagree with this - I usually see smileys replacing periods, not existing alongside them. Your example sentence with "...school. :( I hope..." looks very odd to me. I don't have any sources at hand to back this up, though, which is why this is a comment not an answer. –  alcas Sep 7 '12 at 18:00
    
Thanks for your answer. Having the smiley after the period looks wrong somehow... –  chama Sep 7 '12 at 18:10
    
@alcas Which is why it's a "style choice". Personally, I don't see smileys as replacing periods - that looks odd to me! :) IMO the period should appear before the smiley (never after it, as that corrupts the smiley and is potentially wrong anyway). –  w3d Sep 16 '12 at 18:30
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It entirely depends on the writer. Some use emoticons as punctuation, some don't.

However, I have never seen sentence punctuation after a smilie except when parenthesis (or other brackets) are being used, so I can confidently assert that doing so is descriptively unacceptable even if there are not yet any prescriptive rules.

In my experience, these are acceptable:

I'm glad. :)
I'm glad :)
That's surprising news! (But I'm glad. :) )
That's surprising news! (But I'm glad :) )

while these are not:

I'm glad :).
That's surprising news! (But I'm glad :).)

and this is acceptable, though potentially confusing as the double-parenthesis smilies have additional meanings:

That's surprising news! (But I'm glad :))
That's surprising news! (And I'm sad :()

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With smilies being accepted as parentheses, one will have to be careful to avoid tautology, which I'm glad :) seems disturbingly close to. –  Edwin Ashworth Sep 7 '12 at 19:55
    
Yes. They're deliberately simplistic examples. :) Though, in practice, a redundant emoticon often functions as an intensifier. –  SevenSidedDie Sep 7 '12 at 20:22
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That period after the emoticon sort of looks like a mole on the chin :^). –  J.R. Sep 11 '12 at 23:40
    
@J.R. That seems to be the ambiguity that makes those variations "unacceptable", yeah. –  SevenSidedDie Sep 12 '12 at 1:20
    
@SevenSidedDie: I don't know ~ after all, the mole worked for Marilyn Monroe :^.) –  J.R. Sep 12 '12 at 2:04
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