Keelhauling was a form of punishment for sailors at sea. The sailor was tied to a rope looped beneath the vessel, thrown overboard, and then dragged under the keel and up the other side.

Keelhauling was generally a death sentence since it could take as long as three minutes, and perhaps longer, to walk the ropes all the way back to the stern. Often the ropes caught and dragged on barnacles on the ship's hull: the barnacles ripped the victim's clothing and skin to shreds as he was dragged along.
Dont fuck with me, I'll keelhaul youra ss
by Sallos June 4, 2004
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The unsavory practice of surprising a sleeping partner by running the full length of a sweaty grundle across their nose/face.
After a five hour bike ride, Neil couldn't wait to get home, get out of his spandex, and keelhaul his girlfriend.
by Spjork June 2, 2005
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When a question is posed to the internet at large, not to anyone in particular, and people chime in to say that they don't know the answer. Especially prevalent on technical forums and Amazon Questions, where any given "Does anyone know how to..." will feature many people inexplicably chiming in just to say no, they don't know.

Bonus points if the person is replying with hostility, suggesting that one should not want to know, or to say that they know for a fact it can't be done; triple word score if they say it can't be done, then someone else explains how to do it. Home run if they continue to insist it can't be done after that.

The etymology of this usage refers back to a StackExchange thread where a user asked if the maritime punishment of keelhauling was ever actually historically practiced. Many users replied to say "I don't know" in elaborate ways, often quoting Wikipedia back at the original user, as if he had no access to it himself. In the end, the user did some original research and determined that no, it probably wasn't real. All of the replies were keelhauling.
"Hey, can you get Warcraft 2 running on Windows 10?"
"I've never tried, but lol @ playing Warcraft 2 in 2019. It's real Starcraft hours baybeee!"
"yeah dude okay thanks been fully a week since I had a keelhauling like that but does anyone, like, know?"
by xvicount February 9, 2022
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When having sex, as you're about to climax, Keelhauling involves throwing your partner off the bed and run circles around them while you cum on them.
by Luigi1986 September 29, 2017
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Nauseated, hung-over, especially when the state is induced by copious amounts of Captain Morgan.
I woke up this morning feeling like I had been keelhauled.
by |***Steuer***| December 15, 2010
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A pirate term meaning to walk the plank and send to the depths of the water.
The pirates keelhauled the thief on their ship.
by ShadowM4st3r March 7, 2010
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