A term used to describe a young man who is balding or trying to hide his bald spot—often by wearing a hat. The name “Chicago Hair” comes from the windy reputation of Chicago, where a strong gust could easily blow off a hat and reveal a hidden bald patch.
Man: “Let’s go swimming on the first date—so you cant catfish me with your makeup or filters.”
Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
by yunggravy4 April 22, 2025
Get the Chicago Hairmug. A classic dish from globally renown food capital of the world, Chicago, consisting of 5 lbs of french fries covered in several overly generous dollops of cum followed by a shot of Malort. Ask any Chicagoan what condiment they eat their fries with and they'll tell you CUM. Often considered one of "the classic foods synonymous with Chicago" and "the next best thing since deep dish pizza". Originally popularized on the south side Maxwell Street district.
by Chicago Native Born Boy July 26, 2021
Get the Chicago Specialmug. Tyson: I heard you and Nathan had a Chicago Traffic Jam on Lori}
Wilt: yeah, they were deep in her ass
Wilt: yeah, they were deep in her ass
by Jedi Master Joe September 22, 2017
Get the Chicago Traffic Jammug. A kindergarten sport- During nap time after the teacher has left the room, the chosen boy for the day sees how many broads he can bang before nap time is over before whatever stupid shit video is going on has ended. Rules vary by school district, but sources say this pastime began in Chicago.
Tommy- "Dammit I missed class the other day, who got to play Chicago nap time?"
Brett- "Jason did, he got a score of 5"
Brett- "Jason did, he got a score of 5"
by Synth 2 September 8, 2019
Get the Chicago Nap Timemug. The goody two shoes Saints were crying about cheap shots after getting hit twice by the Chicago Bears. A saint just doesn't have the same effect on an opponent as a bear, a player pulling out a crucifix and telling an opponent they will burn in hell for what they did doesnt have the same effect on somebody as hitting them twice, even if they were sucker punches in the helmet.
by Solid Mantis November 3, 2020
Get the Chicago bearsmug. by SLAYER 💪💪 May 11, 2022
Get the Post one chicago depressionmug. "Johnny boy went and got himself a Chicago Handshake down at Robert's. I'm surprised they have em for only 10 dollars"
by Chris Da anonymous May 20, 2024
Get the Chicago Handshakemug.