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1.
2 or more people having a funny conversation, when 1 or more person thinks the conversation is cool.. they say coolboys. so the people in the conversation are now coolboys.
( in a car, windows down, 9 at night. 4 girls sat in the car with an adult driving )
( boys walking down the road )

a - i wanna bangya (; lol :L
b - phwoarrrrrrrr!
j - FITTYYYYYYYYYS!
m - what time tonight then? :L

b - how cool are we?
a - rather coool (H)
j - we're suchh coolboys ! :D
m - (H)
by happyyyDUDE February 17, 2010
0 1
 
2.
"coolboy" means a boy who is "cool", "in", who likes party life but on the other hand he can´t stand being without sport and his friends and girlfriend(s). Sometimes he is cunning and arch.
You can tell to your friend: "Hey, Mark, you´re realy coolboy"
by pavelkja March 26, 2007
0 3