As a noun, this slang term refers to individuals that are quick to offer a disingenuous handshake and smile. Although interest and affection from this person may seem legitimate, the severity of their fakery can range anywhere from half-hearted respect of social customs to malicious attempts at separating an individual or group from their money and dignity.
May also be used as an adjective, referring to the act of engaging in the above behavior.
Popularized in 1996 by Maynard James Keenan as lyrics in the song Ænema, performed by the band Tool.
When someone says something that may otherwise be mistaken as serious, but follows it with a smiley that helps reduce the tension and lets the second person know it was a joke.
When you save a smiley on MSN Messenger or other and it pops up without it being your intention and ruins your message.
Henrik: The other day my aunt asked me on MSN what she should get me for christmas. I wrote that I had not thought of anything special. When I looked up from my keyboard the P in special had been replaced by a penis.
Eirik: Ooh. thats an Epic Smiley Fail. What did she say?
Henrik: She pretended like nothing, but it kind of ended the whole conversation though....
Eirik: Obviously... And it probably decreased the value of your christmas present by 50%...