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1.
Looking stupid or dumb.
"Did you see Tom, he forgot his lines and just stood there waving his dick in the wind"

"You just left me there, I was there all alone waving my dick in the wind"
by cockshitballs August 03, 2007
 
2.
Looking stupid or dumb. From The Ween Song, Waving My Dick in the Wind
"So I just sat there in the horse costume waving my dick in the wind"

"Look at Tim, he's waving his dick in the wind"
by P.I. Staker August 01, 2007
 
3.
Taking a chance, possibly looking foolish while doing so.
"I'm waving my dick in the wind, waving my dick in the wind
If I make it through the night everything will be alright, But I'm waving my dick in the wind" -Ween
by MostestEverest October 10, 2009