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