Grammar on the Internet: The Parenthetical Emoticon

Most people who use email and instant messaging have used emoticons at some point. What’s an emoticon? A smiley. Like this :) or this ;-) and there are many more.

These types of emoticons tend to obfuscate parenthetical comments within a text. If you are placing an emoticon with parentheses, what then is the proper usage?

First, a couple of examples:

John is a cool kid. (He talks way too much though.) He started a campus student group.

Okay, that is all well and good. Look at what happens when we try to add an emoticon to the parenthetical comment (the words between the parentheses):

John is a cool kid. (He talks way too much though. :)) He started a campus student group.

Note the double parentheses due to the emoticon in the above example. :)) is confusing to look at and might be interpreted as a unique emoticon entity and not the end of the parenthetical comment.

So here are some possible ways the text fragment could be rendered with the emoticon:

1. John is a cool kid. (He talks way too much though. :)) He started a campus student group.
2. John is a cool kid. (He talks too much though. :) He started a campus student group.
3. John is a cool kid. (He talks way too much though. :) ) He started a campus student group.

Which one do you use? Which one is correct? Do you think the comment should be structured differently so that the emoticon doesn’t conflict with the closing bracket? If so, how?

Update: Brian J. suggests a fourth alternative as follows:

• John is a cool kid. (He talks way too much though.) :) He started a campus student group.

This works fairly well, but to my thinking, mixing parentheses and emoticons still is problematic visually.