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Chicago Surprise 

The act of leaving ass pennies around town for unsuspecting pedestrians to find.
I was walking by the Willis tower when I bent down to pick up something shiny. "Wow," I thought, "a lucky penny. My luck is surely changing!" I couldn't have been more wrong. As I drew the penny near my face for a closer look, I could tell that I was being punked. The smell of copper laced with rotting feces left no doubt. I'd just found a Chicago Surprise.
Chicago Surprise by DOTCOM May 9, 2017

Chicago Style Surprise 

This is the Chicago Style Blowjob, Surprise variant.
This time, instead of ya girl giving you a blowjob with you dick in a hot-dog bun with mustard, relish, onion, pickle, tomato, and celery salt, in that order. (But never ketchup, ketchup never belongs on a Chicago Style Hotdog), you put your ween in said bun and surprise her (or him, we don't judge) by sticking the Chicago Style Ween in her puss or Bunghole.
I was feeling a little spicy last night, and you know my girl likes surprises, so I gave her the Chicago Style Surprise.

Michael was being a real d*ck, so I gave him a Chicago Style Surprise he would never forget.
More from Urban Dictionary

Slop Grenade

When someone uses AI to generate a large document, slide deck, or piece of code/software and tosses it over the fence for you to deal with.
Chad: Hey Brent I sent you the new backend API change to review, it’s only 100 files changed.

Brent: he just tossed me a slop grenade
Slop Grenade by Joe Squid September 28, 2026
Word of the Day on September 29, 2026
Short-hand for the word floccinaucinihilipilification, meaning the estimation of something as valueless (encountered mainly as an example of one of the longest words in the English language).
After we broke up, he was floxi to me.
floxi by Dr. Geek May 13, 2009
Word of the Day on September 28, 2026
NYC people who migrate north to Quahog, RI to see the leaves in the fall.
New York and everyone from there can fornicate themselves with an iron stick.
leafers by ss++ February 8, 2005
Word of the Day on September 27, 2026

Respectfully 

Precedes or follows either a gratuitously disrespectful or honest remark, originated in New York City. Used in similar fashion to "no offense" or "to be honest," interchangeably.
Ya mans is wild buns, respectfully. Respectfully he's washed.

After school, The Modells on Jamaica Ave was active. Respectfully.
Respectfully by john quan the first December 20, 2020
Word of the Day on September 26, 2026

You met me at a very Chinese time in my life

A moment in time where you feel distinctly Chinese over all other things.
Dante: "I wish I could be Nigerian, but I can't because I'm Chinese. You met me at a very Chinese time in my life."
Word of the Day on September 25, 2026
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