Top Definition
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 When I looked up from my keyboard the P in special had been replaced by a penis.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%...

Henrik: Damn Msn.
by Mr Ragga N`Chips November 24, 2009
8 Words related to Smiley fail

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