You probably haven't regularly used smileys since your middle school days, when modems screeched and President Clinton rained ordnance against Bosnian war criminals. You've grown up since then, but the ;) has remained inert, a relic of type. In our new modern age, is it ever okay to drop a smiley?
In 1982, Carnegie Mellon computer scientist Scott Fahlman wrote down the first happy and sad emoticons. We know them thusly:
These were thereafter contracted to :) and :( in order to save room, and because that nose just makes you look like a dummy when you use it. All sorts of mutations followed, mapped to our many silly emotions and whims.
At some point we even moved horizontal, saving strained necks around the first world.
With the advent and westernisation of emojis, we've become delighted, cloyed, and spoiled—we don't need to use our imagination (or our keyboards), because there are hundreds of little cartoon icons for poop, hospitals, and various species of marine life.
When you mix technological progress with the passage of time, we look back at the old, textual smileys as quaint and pretty gauche. Kid stuff. Something your grandpa or unwanted aunt uses. A verbal shortcut for idiots, perhaps even below the ever-low hashtag.
But we still see them. We still write them. Is it okay? Is it permissible? Should we stop ourselves?
No. Like the Heyyyyyyyyyyyyy epidemic, the ;) is a necessary dumbing down. We have to act like tweens in order to shoulder our way through the vague weirdness of the internet sometimes, because we're strange creatures who built a strange network filled with strange ways to talk to one another, and dammit we need crutches that aren't strange. The wink is one such crutch. It's a blunt tool, but we're digital monkeys, and we need tools like this.
But bludgeon sparingly. Text winks, when used as anything less than a surgical tool, are similar to peppering your sentences with "like"—you'll sound uneducated. Maybe you are. That's rough. For the rest of us, use them appropriately, in extreme moderation.
For example, a wink with a stranger can be a good icebreaker. It shows that you're not taking yourself too seriously, which can't be stressed enough on the internet. Gawker Media Operations Manager Julia Alvidrez, who I just IMed about this, agrees:
So unless you're being ironic ("man this new company policy is great, I love fewer vacation days ;) "), odds are you're going to try to wink as a means of boning someone else. That's fine. But let's own it, and realize the consequence.
Jezebel alumna and writer for VH1's Best Week Ever Erin Ryan answers the ;) question without pulling punches: "If you want to fuck a dummy, then yes. The winky face is for when you're trying to seduce an idiot for stupidsex." Which makes sense. It's a childlike keystroke, and invokes a youthful "hey, let's touch each other" vibe. Even Jen Doll, resident Internet Word Scholar at The Atlantic Wire, is coming around: "I have long judged the use of emoticons in any communications, casual or professional, but of late I find myself using them more and more, and sort of regretting my judgy-ness." Again, it comes down to what's in our pants: "If you are writing to someone whom you have a crush on—or possibly the opposite—be aware that emoticons can give the impression that you are "trying" and maybe "flirting" too." So don't be surprised if that's the signal you're giving, because you are. You really are. Just make sure you're sticking it in (cough) at the end, as a kicker. The wink should only appear once. Again, just like you wouldn't wink at someone over and over again in person unless you were having a stroke, just tuck the emoticon in at the very end of a message, be it SMS, email, or IM.
Really, you can avoid thinking about this too much if you treat the digital wink like an IRL wink. It's almost certainly facetious—fine for a corny joke—but if executed properly, economically, it can show that yes, you're down to lick someone's face, and you really hope they are too. And a ;) saves a lot more space compared to typing all that gross stuff out.
User Manual is Gizmodo's guide to digital etiquette and internet intelligence.