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chilly willy wumpkins 

Very cold weather. An expression popularised by minor internet celebrity Kunt and the Gang.
Brrrr, it’s chilly willy wumpkins out there!
chilly willy wumpkins by CornhoIio February 10, 2021

Chilly Willy 

To injest alcohol through the nose via snorting, in order to get the alochol into your system quicker. Often done out of the concave bottom of a shot glass.
That chilly willy was fun huh? wait...get up, why are you passed out?
Chilly Willy by Jeremy November 3, 2003

Chilly Williams 

chilly wills... only better ;)

chill=100%
chilly wills=150%
Chilly Williams=199%
"Hey, bro, what you up to?"
"Chilly Williams... you should come over"
Chilly Williams by YuniQ9 January 25, 2014

Chilly Willy 

The most iconic building on the Chicago skyline, the Chilly Willy stands at a towering 108 stories.
Was formerly known as the Sears Tower, but became dubbed the Chilly Willy after Sears sold the tower to the Willis Group, a British insurance brokerage, much to the dismay of the new owners.
Friend 1: Hey Dawg, want to go down to the Sears Tower Skydeck tonight?
Friend 2: Didn't you hear? Sears sold the tower, it's officially the Chilly Willy now.
Guy 1: Hey, how long is the line to the skydeck?
Willis Group Employee: Excuse me, I believe you meant to ask how long the line is to the WILLIS tower.
Guy 1: Hah, Chilly Willy
Willis Group Employee: Please don't call it that
Chilly Willy by countDantes February 4, 2015

the chilly willy effect 

The mind's inability to accept the impossible in fiction.
"There's NO WAY that LITTLE PENGUIN can stomp that HUGE DOG into that TINY CAN! NO WAY!!!" exclaimed Connor (patient zero of the Chilly Willy Effect)

chilly willy 

When one's sex partner sucks on an ice cube, drastically lowering the temperature of their mouth and tongue, prior to giving you oral sex.
LaFawnduh gave me a chilly willy in the bathroom on the bus to Detroit. That's when I knew I was gonna marry her.
chilly willy by dcf68 June 26, 2006