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Canadian slang. Directly related to how cool you are with a certain person. Losing and recieving koolaid points is based on whatever the hell that person feels like.
"Yo, dis weed be da shit. You just earned all yo koolaid points back."
"Omigod, you loser, that sweater is lyke so last season!!!1oneone You just lost all your koolaid points!"
"That Doors shirt is so fuckin' illin. Twnety-five koolaid points."
by loseresque July 22, 2005