If an insertion in parentheses ends with a smiley, how do I distinguish between the two?

It’s the twenty-first century! We have a much better alternative to old ASCII emoticons: Unicode!

A lot of insertions in parentheses (well, if it's not Lisp ☺) can be annoying.

… well, ok, I admit that I do not always like this, either. ☹

Maybe these ones:

:-P)

:-{)

:-()

:-)-:

I'm sure there is not a defined standard as yet, however I find that putting a space between the smiley and the close parentheses makes it look less like a double parentheses mistake (though it can look jarring at the same time :) )

I would certainly, as a pedant, NOT drop the last parentheses (especially where I am not at the end of a sentence :) as it is ambiguous as to whether the parenthesed clause has completed yet, although I would readily admit a mid bracket smiley is particularly jarring and ugly).

I tend to leave a space on both sides, like this

A lot of insertions in parentheses ( well, if it's not Lisp :) ) can be annoying.

also, using dashes is worth trying

A lot of insertions in parentheses — well, if it's not Lisp :) — can be annoying.

Use ٩(•̮̮̃•̃)۶ Unicode smileys

There really isn't any way to make it not look weird (as famously documented by xkcd), but my preferred form, and I believe the more common practice, is to "merge" the smiley with the closing parenthesis. (So, like this. :)

There should not be any spaces after the smiley, in the same way there is no space between a word and a closing parenthesis.

In some messages sent through IM applications, a space is added after the smiley and before a parenthesis, as in some of these applications the textual smilies are replaced from a icon/image; in these applications, the double parentheses are used for a different smiley. This could explain why some people are used to add a space after a smiley, and before the following parenthesis.

In direct conflict with chaos, my preferred form, and I believe the more common practice, is to separate the smiley from the closing parenthesis by a single space. :-)

Normally a space should not be included between a parenthesis and the word it is adjacent to, but when using a parenthesis as part of a separate lexical element, spacing between the "word-element" parenthesis and the "syntax-element" parenthesis is very helpful to avoid confusion. Otherwise you might be sending a double-chin smiley and still have no closing parenthesis.

The best solution, of course, is to avoid such a potentially confusing issue in the first place: grow a goatee, so that all your smileys can be of the form ":-)>".

(what about this (: )

ok... not good enough...

I usually insert the extra space in between the smile and the closing parenthesis for a couple of reasons:

• The extra space prevents unintended tokenizing of the second parenthesis. It bugs me when I write choose (A) or (B) and the text parser converts the capital B and the right parenthesis to a "cool shades emoticon".
• It looks clearer to me. Without the extra space it just looks like my keyboard hiccuped on the right side.

I think James Joyce would go for a dash instead...

A lot of insertions in parentheses - well, if it's not Lisp :) - can be annoying.

I would suggest using a square bottomed smiley with a space after it.

A lot of insertions in parentheses (well, if it's not Lisp :] ) can be annoying.

Think about it this way, how would you do a frowny face?

• A lot of insertions in parentheses (well, if it's not Lisp :( ) can be annoying.
• A lot of insertions in parentheses (well, if it's not Lisp :() can be annoying.
• A lot of insertions in parentheses (well, if it's not Lisp :( can be annoying.

I suggest none of them. Instead you could put the smiley/frowny outside the parenthesis:

• A lot of insertions in parentheses (well, if it's not Lisp) :( can be annoying.
• A lot of insertions in parentheses (well, if it's not Lisp) :) can be annoying.

Thanks to Unicode there's different widths of spaces, some of which may be more aesthetically pleasing depending on your preferences.

Figure Space

A lot of insertions in parentheses (well, if it's not Lisp :) ) can be annoying.

Thin Space

A lot of insertions in parentheses (well, if it's not Lisp :) ) can be annoying.

Hair Space

A lot of insertions in parentheses (well, if it's not Lisp :) ) can be annoying.

(Note: some render at different widths depending on font, so experiment with fonts if none of these are satisfactory)