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The Pineapple Club

Cheech: "Yo, are you a member of The Pineapple Club?"

Chong: "I'm not sure. What is it?"

Cheech: "I don't know, but i'm a member according to r/trees"
The Pineapple Club by ips1023 September 9, 2010

Massage the Pineapple

Its when you grab your penis and smack it till it does something. For maximum damage think of girls while doing it.
I just saw a member of the opposite sex, i'm going to massage the pineapple in that public toilet over there. Cheerio.

putting the pineapples away 

I was putting the pineapples away in the toliet cause she wasn't puttin out.

riding the pineapple 

On the government dole (tab): on welfare, illegitimate disability, etc.
Connie lied about her MS, and started riding the pineapple.
riding the pineapple by dghost September 7, 2011

Poke the Pineapple 

When one uses their phallus to poke another person's butt cheeks, but ends up prodding their sphincter instead
Person 1: Did Barry "poke the pineapple"?
Person 2: Yes, and he took our friendship to a whole new level...
Person 1: So he's out of the friendzone?
Person 2: Unfortunately yes

Ride the Pineapple Express 

A way to say “Let’s go smoke some weed”, based on the 2008 movie Pineapple Express.
Person A: Yo, let’s go ride the Pineapple Express!

Person B: Sick! I’ll go get my bong then.