1) To have something backfire to the point where you are embarrassed and humiliated.

2) To do something that ends up going nowhere, or, in a worst-case scenario. ends up being a step backwards in the wrong direction.
John was trying to prove to his brother Roger that he knew how to repair a computer. After he somehow installed a massive virus into Roger's computer, having the hard drive compromised, overheating the motherboard, and having to pay for the costly repairs, his efforts ended up with him pissing in the wind
by Mr. Lefty July 20, 2014
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An alternative way to sing the Bob Seeger song "Against the Wind", especially if it's 3:00 a.m., and you're drunk.
by MRT3 July 2, 2009
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Messier than swimming against the tide.
Skip to the loo, pee to the lee, my darling. Don't piss in the wind, you'll spring a leak in the dinghy.
by Horace Hornblower July 29, 2008
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go take your futility elsewhere. Your opinion was unfair.
Her: "watching you shove your personal angst into good poetry is like watching a fat woman trying to squeeze herself into my favorite dress."

Him: "Go piss in the wind."
by ALGGG January 18, 2008
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when you take a piss outside and it moves I the wind
yea joe took a piss in the wind yesderday
i heard it went all over his pants because the wind blew it back at him
ROFLMAO!
by YouWatchHentaiYouHornyBastard0 September 25, 2016
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