Chilly Boy 

A man who does everything right and wrong at the same time; breaks rules that are meant to be broken

*bartender serves a generous pour* “he must be a chilly boy”

Chilly Boy by JAAAA! January 6, 2023

Challyboy 

A term used for a stereotypical Dr Challenors boys school student.

The typical Challyboy will be the following
-Tall height
-Pasty, freckly and the majority of his body covered in acne, especially around the up pointed nose.
-Extremely Racist as are from upper middle class families with no culture or outside life.
- Pick on the weak, even of their own breed of challyboy have no understanding of the word empathy other
- Closet Homosexual as are restricted from female contact
-if not homosexual, terrible at talking to women. (usually stare and perve.)
-bad at sport other than pollo and fox hunting
-Unpleasent to look at and smell
-Walk with a hunched back, nose high in the air as possible ( the alpha male challyboys can dislocate their neck to show their "superiority") and usually in a zigzag as are unable to walk straight.

Why be a sailor when you can be a Challyboy?

Challyboy by Challenorsnob September 6, 2010

ChallyBoy 

A ChallyBoy is a boy who goes to Challenors Boys School and:
A) Thinks he is the shit because he is able to pay for people to like him.
B) Has a superiority complex because people as a whole regard ChallyBoys as really smart, but as a whole people are retarded.
C) A homosexual who is afraid of girls.

A)ChallyBoy: If you blow me u can have a ride in my porsche
B) Paul McKay
C) Peter Cant

ChallyBoy by Scorerrific July 20, 2004

ChallyBoy 

Correction, a chally boy is a boy that goes to challoners. Just cos they have an I.Q higher than their age (unlike the fucktards who started this entry) they get picked on. They are not rich, just smart. Plus we dont need to meet girls at school, thats what partays r for. Stupid kevs.

"Just cos those chally boys are smarter than you, you feel threatened."

ChallyBoy by Moose Lord July 8, 2005

ChallyBoy 

A term used mostly by the Amersham School, and similar schools in the area, because they want to look cool and hard for being stupid, but are actually retarded pricks who can't get a job because their own school is too shit to teach them properly.

HAHA ChallyBOY! (out the window of a car) Oh shit my dick just fell off.

ChallyBoy by PekingDuck8 March 28, 2010

chillyboo 

A girl who is like a bromigo but is a girl

guy1:"Ima go hang with my chillyboo"
guy2:"Are you gay? that is the second dumbest thing i heard today"
guy3:"I think your dumb cause there are very few chillyboos out there man just grow up and accept the fact that he has an awesome girl to chill out with just chill a bitch"

chillyboo by proboss September 10, 2011

Chillybob 

A self-loathing gay guy who throws around f slurs to seem straight, but he is not fooling anyone.

I'm Chillybob. I love sucking cock, but I am not a fag!!!

Chillybob by Chillybobisgay4real February 28, 2025