Emoticons, also known as smileys, can refer to two things. First, they can refer to the use of punctuation and other characters to depict facial expressions, as in :) :D :( D:< etc. Secondly, they can refer to the little images (generally GIFs, sometimes animated) that software often swapped such character combinations out with. In the era before emojis, these are what everyone used instead.

History of Emoticons

Emoticons are generally considered to have been invented in 1982, by Carnegie Mellon computer scientist Scott Fahlman. They were a response to the fact that it was difficult to convey tone in text, so :-) was coined to mean “you should take this sentence as humorous” and :-( was coined to mean “this is serious”. When the internet started becoming mainstream in the 1990s, this original intention was lost and the smileys attracted the straightforward “happy”/“sad” meanings they have today – and a large number of other emoticons were coined as well.

Japan has a separate lineage of emoticons, called kaomoji (which has its own section later on this page). These were apparently first invented in 1986.

Emoticons seem to have fallen into disuse as emojis have got more and more software support, and therefore become mainstream. Emojis have some technical advantages compared with the image-based emoticons (e.g. being included in Unicode, so you don’t have to rely on some forum software substituting character combos with images, nor worry about it replacing a combo you didn’t actually want to become a smiley – this happened very often with lists if you had an item 8) or b) (as it would match “B)”). Also, a lot of the original emoticons were pixel art that now looks blurry on Retina or HiDPI monitors. However, I think there’s something charming about the original emoticons, and certainly nostalgic. There are still some that haven’t yet seen a real emoji equivalent (although the number has shrunk as more and more emojis have been added). Indeed, the emoticon :P rarely got a good depiction even in the image days (:P is not smiling, come on!).

Text-based Emoticons

As mentioned, originally, emoticons like these included a hyphen in the middle to represent the nose (like :-) or :-( or whatever). I always thought this was ugly and I never included the hyphen, myself. So, with that in mind, here’s a quick run-down of the emoticons I remember using (and in some cases still use occasionally), together with a keyword for what I think the key meaning is. I’ve grouped synonymous ones together.

  • smile — :) =) ^_^ (:
  • wink — ;)
  • sad — :( =(
  • single tear — :’( ='(
  • sobbing — T_T T__T
  • grin — :D =D
  • oh no — D: D=
  • tongue out — :P =P
  • ironic tongue out — ;P
  • laughter — xD XD
  • disgust — xP XP
  • annoyed — >:(
  • angry — D:<
    • also I think MSN Messenger put its angry emoticon at :@ and sometimes on forums etc. it’d be at :x, so you’d see these too, but if I saw them just in text I wouldn’t immediately think “angry”
  • evil grin — >:D
  • surprise — :o :O O_O
  • cute — :3
  • angel — 0:)
  • vampire — :K
  • unimpressed — :| =| -__-;
  • uncertain — :/ :\ =/ =\
  • confused — :S :?
  • kiss — :*
  • cool — B)
  • nerd — 8)
    • a lot of forum software translated “B)” and “8)” to the same image though! I think to a lot of people they were synonymous, and could variably mean “cool” OR “nerd”…
  • weirded out — o__O
  • dead — x_x X_X
  • vexed — >.<
  • who, me? — >_> <_<

Image-based emoticons

Depending on what website you were on or instant messenger you were using, there were lots and lots of different emoticon sets still out there. Below I’ve included a few of the sets that I saw most often, but there were loads and loads of different sets. You could even go and download random smiley packs off the net and plop them in to replace (or supplement) the default smileys of your chosen instant messenger, blog or forum.

  • phpBB: icon_smile icon_wink icon_sad icon_cry icon_eek icon_biggrin icon_mrgreen icon_lol icon_razz icon_mad icon_evil icon_twisted icon_rolleyes icon_neutral icon_cool icon_confused icon_surprised icon_redface icon_arrow icon_idea icon_exclaim icon_question
    • This is the OG set, anyway; it seems like phpBB later revamped their emoticons to give them all angular chins. This set was used really widely across forums (even forums that didn’t run phpBB!) and Wordpress blogs.
  • vBulletin: smile wink frown mad eek biggrin tongue cool redface confused up down
    • The vBulletin emoticons were definitely less common a sight than the phpBB ones, with the exception of the “???” emoticon. That one (or at least one with the same design) was everywhere.
  • Neopets: smiley sad oh sunglasses vampire yarr angel angry complain lol grin cry winking facepalm cough clap tongue unsure violin kisskiss
    • I spent a lot of time on Neopets as a kid, plus again for nostalgia reasons between 2016–19, and these are the smileys you can use on the Neoboards and in guild discussions (plus there are others for Neopets-specific things). Where did these come from? Why do they seem to come from two entirely different sets of smileys?? No one knows. Well, someone probably knows, but I don’t. Anyway, this set includes a number of useful emoticons, like “:K”, “cough”, “clap” and “facepalm”.

And as a teenager in the 2000s, I was certainly familiar with the emoticons used in MSN Messenger. Here’s a graphic showing a number of them (pre-2010 revamp because apparently that happened): 40 MSN Messenger emoticons; the art style is definitely not flat, with shaded yellow faces


Japan developed its own style of emoticons, which involved the smileys being oriented right way up instead of sideways. Some of these did spread to the Western internet, and therefore I included them on the list above. Some of these are: T_T, -__-; x_x, >.<, o__O and ^_^. In Japan, they’re often surrounded by brackets, e.g. (T_T) or (^_^). The number of underscores can be variable, but would usually be one or two, with more than that used for emphasis. (Like, if you see o________________O, someone is REALLY weirded out.)

The examples I cited are relatively simple; a lot of other kaomoji require special characters (that don’t appear on a basic Latin keyboard) to type. Some examples of these are: ( ͡° ͜ʖ ͡°), (¬‿¬ ), (づ ◕‿◕ )づ, ¯\_(ツ)_/¯

In iOS, if you use the default Japanese keyboard layout, there’s actually an in-built menu to paste all these kinds of kaomoji. You also do see them reasonably often in Western discussions online. But I’m sure in Japanese discussions you’d see a lot more, and a greater variety, too.

See Also / References