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Playing Chess 

1) Drinking heavily
2) Ordering drugs from a dealer
3) Obscure pseudonym for anal sex
1)
Person 1: Dude, where's your dad?
Sonofadrunk: Playing chess.
2)
Person 1: What were you doing in that back alley?
Druggie: Playing chess.
3)
Person 1: What were you and that other guy doing in the locker room?
Gay dude: Playing chess... heehee!
Playing Chess by AdurnaVampyre January 26, 2009

playing chess 

Slang for ordering a bag of drugs from a dealer. Used to ensure secrecy when talking over the telephone.
"Hey man, I was hoping I could come over and play chess today."

playing chess 

drinking, usually heavily.
coined by underage kiddos to avoid detection by their mothers and other authority figures.
often used ironically or obviously - whether the kiddos are aware of this or not.
Hey, let's steal some beer from Chris's parents and play chess.
playing chess by Annie October 13, 2004

playing chess with the pope 

Playing chess with the pope sounds like the classiest way possible to spend your time. Unfortunately, in Iceland, it doesn’t mean enjoying a dignified pastime with a religious leader, but rather is a polite way to say you’re “going number 2”. We have no information on the pope’s thoughts on the matter, nor his abilities as a chess player.
Question: Hey, where is Michael?
Answer:Probably playing chess with the pope.(taking a shit)

Playing chess with the poltergeist 

When you stay up during the witching hours playing chess by yourself because everyone is sleeping or far away from the scope of control.
Person 1: "sorry man i cant stay up any longer, i'm too tired."
Person 2: It's ok, i'll be staying up Playing chess with the poltergeist That'll keep me busy."

Playing 5D Chess 

suspiciously trying to deceive one or more people in layers of deceit, either on purpose or suspected by someone.
John: Steve is totally acting sus, he knows we suspect him but what if he's trying to look guilty on purpose so we don't think it's him, but then that would be a reason to think it's him.
Hank: I agree, Steve is seriously Playing 5D Chess with us.
Playing 5D Chess by 岸谷新羅 September 28, 2020