The Smiley Face Dilemma: Using (and Abusing) the World's Most Popular Emoticon

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Image by Lizzy Acker

To be honest, I've never been one for smiley faces. I've always felt I am just like one year too old for them. At my brother's high school graduation I listened to a popular teacher give his whole speech on the scourge of emoticons and I thought, "really, this is a thing that happens?"

My brother is 13 months younger than me.

Anyway, I resisted the lure of the emoticon for a long time. I'm a writer, allegedly, so why couldn't I just use words to express my feelings? Or if a facial expression was required, why not just find the person I had an expression for and smile or frown at them? But like any trend in language that English majors decry--the preposition at the end of the sentence, saying "me and Steve" instead of "Steve and I"--the pull of the smiley was hard to resist. More and more of my communication started being in short written sentences: chats, texts, emails. I started being friends with AND RESPECTING several heavy smiley users. And because I am the kind of person who frequently does the exact thing she said she would never do, I decided to throw myself into the world of expression through colons and parenthesis and see what happened.

After much intense, personal research on the subject of the most popular of all the emoticons, I have come up with the following findings:

Contrary to popular belief, it's okay to use smiley faces in work emails. SOMETIMES.


Strangely enough, work was my gateway drug into emoticons. Here is the problem at work that the smiley has solved for me: that moment when someone has sent me an email thanking me for something I have done for them and I can't decide if I should respond or just leave it because there really isn't anything left to say but if I just leave it, will that be misconstrued as rude? Will the colleague think I am ignoring them or I don't care that they said thank you? Recently, I stopped freaking out and started responding: ":)"

Similarly, the smiley face works in the situation that an email chain is going on too long for any reason and needs to be stopped. At work, 🙂 means "The End" (please see exceptions to this rule about four paragraphs down).

Stick with the classics.

A warning about work email: Outlook changes the simple 🙂 into a symbol that people outside of Outlook see as a "J."  This gets confusing (one co-worker told me he thought I was just really bad at typing for months before he figured out what was going on) so it's best to just undo and make it a straight up colon and closed parenthesis. The same can be said for basically all Emojis on the phones of people who don't get Emojis. They look like alien bugs in swimsuits. My experience is it is best to save Emojis for silliness and Instagram comments. Someday we will all implicitly understand the meaning of baby frog face, side eye and ice cream cone, but for now those things can mean roughly anything and before you know it, someone will be breaking up with you because of your  weird skin condition and you will think they are just asking if you want to eat pizza for dinner.

Are you asking me to move out or to go surfing in Hawaii? WHAT IS HAPPENING?!

Boys like to use smileys as much or more than girls.

Though some people might think "teen girl" when they think smiley face, in my experience it is actually boys, actually MEN (I'm trying to refer to my male peers as "men" now that I am in my thirties), who rely on the smiley in text. As one friend told me: "I'm worried I'm going to sound like an ass without a smiley face." This idea seems to be the real driving force behind the use of the smiley in short, text-based communications and I am developing a theory about this: men and women communicate way differently, and in real life (IRL, if you're a kid), men are, either through socialization or whatever, taught to be more direct than women are. In real life, sometimes this gets them into big trouble with the ladies. Like "oh no that girl is crying and all I wanted was for her to park the car correctly without killing us and how did this happen oh my god I don't want her to be crying!"-type trouble. In real life, when one of these gender miscommunications happens, a guy can apologize and give you a hug, because honestly, he hates it when you start crying ("you" equals me in this scientific study). Over text, boys cannot see your face. They cannot see if you are crying. They don't have the heavily attuned telepathic reflexes of those of us raised as women, who have to judge how other people are feeling at every turn, in millions of contexts, based on the tiniest clues. To combat this fear, that somewhere a girl is sobbing as soon as she reads their texts, nice boys like to use the smiley face. And that's okay. It's kind of cute actually.


However, there are many, many occasions when a smiley face is not appropriate.

As my unimpeachable evidence suggests, smiley faces have a time and a place. They are disarming and they can be used to represent a smiley feeling behind the surface meaning of whatever words you send over the internet tubes or whatever magic gets your texts sent to your friends. But, like any form of communication, they can be misused, and they are, frequently. Here is an incomplete list of the times when you are NOT UNDER ANY CIRCUMSTANCES to use a smiley emoticon. Also, please note, you are not allowed to use a 😉 (winky face), a 🙁 (frowny face) or a :/ (ambivalent face) in these situations either.

1. Death of any kind. Even a dog. Even a cat. Even a hamster.
2. Reporting STDs.
3. Any possibility that you will be breaking up with the recipient of the smiley within the next 12 hours.
4. Quitting your job.
5. Cancer.
6. In response to any of the following: a long phone call, a tearful IRL interaction, an email longer than two paragraphs or which contains anything remotely emotional, an actual letter, a job offer, a wedding invitation, an interview request.
7. Friend's divorce.
8. Announcement of pregnancy: anyone's, including yours. Wanted or unwanted.
9. In a work context that is not one stated above AND/OR is with someone who you have not met IRL or you know is anti-smiley or two levels or more of boss above you.
10. During a fight.
11. When admitting to destroying someone's property.

Sorry/not sorry for ruining your favorite item of clothing!

It's a good rule that when actual face-time is needed, a smiley will not suffice. And if there is a chance that your smiley will come off as dickish or passive-aggressive at anytime in the future when your audience of one is pouring over your writing, searching for meaning, best to just use your words/your voice/your real-life smile.


So what do you think? Are smiley faces allowed now? And what is your worst smiley face experience? Tell me in the comments. See you there 🙂

You're kidding, right?