a sideways representation of a smiling face, :‑), or similar combination of symbols, as ;‑), a winking face, or :‑(, a sad face, created by keystrokes and used to communicate humor, sarcasm, sadness, etc., in an electronic message. Compare emoticon.
smil·ey (smī'lē) n.
pl.smil·eys An emoticon, especially a smiling facial glyph [ :-) ] used to express delight or to indicate humor or irony. adj. Having a cheerful and happy disposition; smiling.
n. a circular, smiling yellow face. (The face appears in many forms: stick-on labels, pin-on buttons, hand-drawn, etc. It is possible to re-create the smiling face on any keyboard through the use of the punctuation symbols, as with :) or :-). All computer Smileys and their variants appear sideways. A major variant is the Unsmiley, which is basically :( or :-(. The following faces are a sample of the variants that can be seen in computer forum or news group messages and informal typewritten or word processed notes. This type of symbol is called an emoticon because it is intended to show emotion in what is otherwise a rather cold medium of communication. The typical use is to show that the writer is just joking or writing in good, well-intentioned spirits. Recently, more complex graphics have allowed actual smiley face versions of many of these variants to be inserted into the text. The following Smileys are separated by slashes, and an equal sign separates the actual Smiley from its explanation.) :-] = Squarejaw Smiley / :-o = Singing Smiley; Shocked Smiley; Surprised Smiley / :-( = Sad Smiley / :-) = Happy Smiley / : -=) = Smiley with a Big Mustache / :-)' = Drooling Smiley; Smoking Smiley / :-)8 = Smiley Wearing a Bow Tie / :-D = Big-mouth Smiley / :-# = Smiley with Sealed Lips / :-* = Pursed-lips Smiley; Shocked Smiley / :-s = Twisted-mouth Smiley (after hearing or saying something strange) / :-“ = Smiley with Walrus Mustache / :-| = Smiley Making Dull Response; “Have-a-dull-day” Smiley / :-> = Wry-faced Smiley / :-0 = Loudmouth Smiley; Big-mouth Smiley / :-x = Sealed-lips Smiley / :-Q = Smoking Smiley; Drooling Smiley / :> = Midget Smiley / ;-) = Winking Smiley / (-) = Smiley Needing a Haircut / “:-) Smiley with its Hair Parted in the Middle / +:-) Smiley Priest / *-( = Smiley Cyclops, Poked in the Eye / *:o) Bozo Smiley / <:I = Dunce Smiley / @-) = Cyclops Smiley / @:I = Smiley Wearing a Turban / |-) = Gleeful Smiley / |-| = Sleeping Smiley; Bored Smiley / 0-) = Smiley Wearing a Scuba Mask / 8-) = Smiley in Glasses / 8:-) A Smiley with Glasses on its Forehead / B-) = Smiley Wearing Horn-rim Glasses / o-) = Cyclops Smiley / [:-) = Smiley Happily Listening to a Walkman / [:|] = Robot Smiley; Squarejaw Smiley Listening to a Walkman. :
Dictionary of American Slang and Colloquial Expressions by Richard A. Spears.Fourth Edition. Copyright 2007. Published by McGraw Hill.
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noun, plural ‑eys, adjective 
[smahy-lee]