I’ll admit it – this has been bugging me for a long time.  I’m no punctuation guru and none of this applies to formal writing, but I really need to know the answer: In emails, social network posts, and blog comment posts, if I write a sentence and place a smiley at the end, does it need further punctuation or not? And where do I put it?

FYI: I’m putting spaces in between the characters so that WordPress does not change them into real smileys.

I love it! : ) (Maybe…)

I love it : )! (I hate this one.)

I love it : )  (A little voice is screaming for something more.)

How about when it’s in parentheses?

I read your book (loved it : )) and have a question .  (Ack!)

I read your book (loved it : ) ) and have a question.  (Nope.)

Okay, so you might think I’m picking nits here, but I’m not the only one. Searching the internet, I found over 93,000 articles relating to this question.

It seems there is an unofficial solution.  If a smiley is at the end of the sentence, one should replace the end punctuation with the smiley.

     I love it : )

If the smiley is in parenthesis, substitute, though the opinions on what to use as substitutions vary as well:

I read your book (loved it : ]) and have a question.  (Yuck!)

or

I read your book (loved it : D) and have a question.

or

I read your book [loved it : )] and have a question.  (I think I hate this, too.)

During my search, I found Netlingo, which lists many more smileys than I ever knew existed. For example, Teletubbies have their own smiley -(:)(0)=8  (never thought I’d be mentioning a Teletubby in one of my blogs) and someone with a mustache and beard would be {:-{)}  My puppy should be referred to as <(-‘.’-)> (look at that one straight on, not sideways.) And here is a scuba diver with hair )8-)

Placing the usual punctuation at the end of a few of those sentences might confuse things, and I think it is possible that I’ve been spending way too much time editing my book – my hand is itching to put periods in.

Maybe rewording the sentence is in order?

     <(-‘.’-)> refers to my puppy.

Okay, now I’m having trouble because I’m not capitalizing the first letter.

     This <(-‘.’-)> refers to my puppy.

Much better… but thinking about all this takes time and with most popular social media, time is not an option.

Maybe I should stick to email?