Top Definition
A rhetorical question asked to indicate that a person has been thoroughly schooled, reamed, or taken to the house. Pretty much means, "That must have hurt!"

A short, more polite form of, "How's your cornhole?" To make it less offensive/obvious, you may add "...family" or something similar to the end of "How's your hole?"
Banker 1: "I'm in equities, what do you do?"
Banker 2: "I'm in subprime mortgage trading?"
Banker 1: "Ooooh...how's your hole?"

Prisoner 1: "Man, I dropped the soap again last night."
Prisoner 2: "Ooooh...how's your hole...family?"

Yuppie 1: "I just got hit up for $5 on this half-gallon of organic milk and $10 a pound for this free-range chicken at Whole Foods."
Yuppie 2: "Ooooh...how's your hole...foods?"
by Nicholas D November 19, 2007

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