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
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
The team people are thought to be insane if they root for after over a hundred years of no titles or championships, and people still root for them anyway, because winning is not the point of everything in life.
Not many other sports teams would keep people rooting for them after not winning for so many years, a lot of people would abandon a different team than the Chicago Cubs.
by The Original Agahnim July 01, 2021
When some idiot doesn't clean the snow off the roof of their car either because their ignorant or were in a hurry and when they stop fast it flies backwards on your windshield blinding your field of vision instantly as they drive away laughing.
ThatJag-Off just got me with his Chicago luggage lazy bastard! Good thing I didn't wreck my car or it would of been his ass!
by Ol watchmen January 12, 2024
by James Westen April 19, 2019
A good luck pre-game ritual for Chicago White Sox fans where your girlfriend slips on a black sock (normally used for feet) on your cock and jacks you off until you cum into the sock while you sit back, relax, and strap it down with a beer, preferably a Miller lite (or modelo if your girl is Latina)
This is similar to the Clark Street Cock Sock, which is performed exclusively among men within the gay community and into a blue sock before Cubs games instead.
This is similar to the Clark Street Cock Sock, which is performed exclusively among men within the gay community and into a blue sock before Cubs games instead.
My girl surprised me with the ole Chicago White Sock before the game that was so good I nutted through the sock and Giolito threw a no-hitter!
by DamnGoodCockSock April 01, 2021
Four Steps: Go to a strange place with no sleeping arrangements, find a girl, bang her, then stay at her place.
by jugghandler March 28, 2016