wink-frown 

;(

A feat that is impossible to accomplish. And if you do you just look dumb.

Katie just tried to wink-frown at me... and failed.

wink-frown by Timfimwa April 23, 2008

Winkfrown 

An emoticon used to signify sadness, with a bit or sarcasm or cynicism, or humor. It's like saying "tragic, but you get it".

;(

In an online chat, adding a winkfrown:

"Ya, she was really happy to be there,
until she broke her ankle! ;( "

Winkfrown by Tattered Hoody August 10, 2009