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An urbanized and supposedly cool way of saying, "That's the way the cool crumbles." Mostly used by perverted pre-pubescent boys who think the quote is sexual.
"Aw man, I just got a D on my math test.." "That's the way the pickle squirts dude."
by Erika June 1, 2004
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Forest Gump: "Life is like a box of chocolates...(takes bite out of piece of chocolate)...you never know what you're gonna get."

Me: "What a fucking stupid idiot, but, I guess that's the way the cookie crumbles."
by Tim Jerome March 18, 2008
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cookie represents an object of desire. the state of crumbling represents that the object of desire is no longer attainable in its desired form, or that the object of desire has reached its culmination within a state of decline.
High school senior: "I wasn't accepted into my top choice university."
Father: "Sometimes that's just the way the cookie crumbles."

Boy: "My girlfriend and I finally broke up. We had been arguing for weeks."
Friend: "That's the way the cookie crumbles."
by Zach Herold November 23, 2006
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The angle of the trajectory of pickle fluids when a is squished.
The pickle squirted at 38.256° above the horizontal.
by DragonlordALS May 28, 2004
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A phrase meaning, basically, "That's the way things are, you cannot change it". Usually said to calm someone who's whining overmuch, an usually with little effect.
Man 1: I went on vacation and my fern died!

Man 2: That's the way the cookie crumbles.
by Daniel Finetail May 26, 2004
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As if to say "That's how life rolls." It's also a good response for when somebody says something you don't know HOW to respond to. It's also just a cute thing to say.
1.
Girl. Classic vegetable is better than chicken noodle.
Boy. No it's not.
Girl. How?
Boy. That's the way the cookie crumbles!

2.

Boy. Your eyes are beautiful.
Girl. Uhm...that's the way the cookie crumbles!

3.

Boy. You're so weird lawlz.
Girl. That's the way the cookie crumbles.
by tooswoleforyou666 August 3, 2011
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