to sell your soul or bet it by basically risking your life for anything
1 way: Rondo will gamble with your soul. 2nd way: i cant take this i need her i have to gamble with my soul.
by LilDurksGrillz January 14, 2021
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When you're not sure whether its a fart or a turd, but you go for it anyways, you are embarking on the Poop-Fart Gamble.

If you win the gamble, you've only farted. If you lose, you just shit your pants.
I lost the poop fart gamble today at work. I had to waddle to the bathroom and ditched my boxers in the garbage. Fuck.
by honkbert March 15, 2008
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A box of chocolates arranged in random order. They are usually bought on Valentines in a box the shape of a heart. There are several pieces of chocolate that all taste different. When you take one chocolate and eat it, you have no idea which ones are good or nasty so you gamble on which chocolate would be the good one. So before you even touch one of them, its going to be a big surprise. If you pick one thats so nasty that you have to spit it out, you lose.
I just got some gamble chocolate and unfortunately, I bit into the one with toothpaste.
by tatomuck1 April 11, 2009
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Making a bad meme that earns gold
Welcome back to "Reddit's golden gamble," the game show where you post the worst meme you can and see how much gold the audience awards you
And the daily winner of reddit's golden gamble goes to...
by ♥🗺☠ August 4, 2021
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It is when your woman is doggy style or bent over the bed, ass in the air. You lube or Vaseline her hips and crotch, entirely. Then do the same to yourself with your choice of delight enhancing solution for your Greasy Gumble.

Then, position yourself across the room, as far away as possible while still being lined up with your partner. After achieving a full errection, use viagra if you wish but is not suggested. Then without warning, take full stride towards her all while screaming "GREASY GUMBLE GAMBLE!" As many times as possible.

The full point is in the gamble on which hole you end up inside. Or, possibly none even at all. Risk of serious injury is possible.
'thebestman' asked his woman to 'Greasy Gumble Gamble' with him. "It could be fun!", he added.

The 'Greasy Gumble Gamble' can be chill to try. Just don't attempt to Superman on your way in. "Your gonna have a bad time!"
by The True Addendum March 19, 2016
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not to be confused with the recently popular movie "John Tucker Must Die", a john tucker gamble is the sweetest, most genuine, sincere, and greatest person in the whole world. Note, both jt's share the same the trait of their smoking hotness and inability to control the ladies affinity towards them. Never the less no one lady loves a JT Gamble more than his best friend in the whole world. (see jordan paglia)

Note; a john tucker gamble is never complete without a wonkey eye when photographed and the always overwhelming urge to give it in the butt.
-"I met the perfect guy the other night, he is the man of my dreams, gorgeous, sweet, and amazing."

-Back off! that's my john tucker gamble!!
by jp :) June 5, 2009
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