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The Chicago Woodsman

The act of defecating on the back of your one night stands head before leaving their house in the middle of the night.
Mark: Did you hear what happened to Steve Last night?
Jenny: No....Is he OK??
Mark: Yeah, just got The Chicago Woodsman from his one night stand
by The Real Woodsman September 13, 2023
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Chicago

it’s a city that inviting it’s a city that’s exciting it’s a city for a woman just like me!
trina vega: CHICAGO! CHICAGO!
people watching at home: ITS A CITY THAT INVITING ITS A CITY THAT EXCITING ITS A CITY FOR A WOMAN JUST LIKE ME!
by Scree December 10, 2019
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The Chicago Bear

The Chicago Bear is when you have received a Green Bay Packer rectally, from the Bear variety of men; you then find a football field and just shit all over it.
"In Illinois, people of large numbers gather in a stadium to watch local heroes perform The Chicago Bear, in person."
by Verbius VonMasturbate August 12, 2021
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Chicago Soft Serve

I pranked Sam so hard when I gave him my Chicago Soft Serve
by JustLib July 17, 2022
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The act of a woman giving a blowjob using the back of her hands, after she eats pulled pork and beans.
"Did the Chicago Back-hand BJ with extra hogslop meant nothing to you?"
by ToolFan5878 November 7, 2025
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An idiom used to explain how a seemingly negligible or "weightless" variable can have a massive, tangible impact on an outcome.
It refers to the physics concept of radiation pressure. Because light carries momentum, the sunlight hitting a city like Chicago on a clear day actually pushes down on it, adding roughly 300 lbs of physical force to the city's total weight.
Example 1:
Person A: "I only changed a single line of code and the entire server crashed. I don't get it."
Person B: "Chicago weighs more on a sunny day!"

Example 2:
Person A: "I barely touched the gas pedal and we spun out!"
Person B: "Chicago weighs more on a sunny day, man."

Example 3:
Him: "She broke up with me just because I didn't hold the door open?"
Her: "Chicago weighs more on a sunny day."

Example 4:
"If I had found my keys ten seconds faster, I'd be here. Chicago weighs more on a sunny day."
by anonymous202997 December 4, 2025
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Chicago Waterboarding

When someone holds a shot of Malort in their mouth pulls their shirt over their face and has someone pour Gatorade on them.
Man did you hear Tony almost died from one too many Chicago Waterboardings
by James "charles" Whirlpool December 30, 2019
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