This might seem like a silly question, but this situation happens all the time during virtually any type of online correspondence. It's quite common to put something friendly/funny/tongue-in-cheek in parenthesis as an aside, and it's also often important to include the smiley to let the other person know you're being funny, so it's irritating to not know how to combine the two and make it look right. I often end up with rather unfortunate scenarios like this:
... but sometimes people here just drive me nuts (not you, of course ;) ).
I've seen people use a single space like above (perhaps the most common), no space at all, use square brackets instead of parentheses, and also incorporate the smiley into the closing parenthesis.
So, what's the best way to handle this?
P.S. We probably need a parentheses tag...