When you're masturbating and you accidentally pop the cherry(make your cum burst out of the top making the cum hurt when it comes out)
Coy:hey dude are u okay?
John:I think I may of made my pickle pop last night...
Coy:that must of hurt..
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when a male has lost his virginity. similar to when a girl has popped her cherry.
hey mitch, do you have a popped pickle?
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The phrase used to confirm something when you are moderately indifferent to the actions of a friend who's mental faculties are questionable.
Person 1: So Im gonna ask Grey to marry me today.
Person 2: Didn't you just meet?
Person 1: So?
Person 2: Whatever floats your boat, tickles your pickle, pops your peach
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A green penis on a stick. Preferably in the cold.
Torah; "it's cold outside"
Sasha; "I wonder if any boys have a pop pickle"