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Smiley fail 

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 When I looked up from my keyboard the P in special had been replaced by a penis.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.
Smiley fail by Mr Ragga N`Chips November 24, 2009
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failed smile

The look that you get when you know you are defeated or have failed.
When Sasha Cohen won the silver medal at the Olympics after falling in her program and losing any hope of gold, she got failed smile.
failed smile by Sean Bloodgood July 21, 2008