shaving a snake

doing something that you know will not turn out well.

Bill: I heard tom was going to have sex with karen tonight.

Billy:doesn't she have an STD?

Bill:yeh, man he's totally shaving a snake.

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Trying to Shave a Snake

A phrase coined by Demetri Martin.. It is used to describe a situation that doesn't work out well, just like shaving a snake. It's just not going to happen.

"You hear Jerry's trying to open that Frozen Yogurt business?"
"Good luck to him.. If you ask me, he's trying to shave a snake."

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