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This is a challenge for all the Italians or Italian-looking people out there. Basically you have to score a threesome with an Italian girl (from Italy) and an American girl. The kicker is that you have to convince the American girl that you're Italian while convincing the Italian girl that you're American. Extra points if you get 'em both indabutt. The best strategy is to speak bad Italian and broken English and make sure the American girl doesn't know Italian and the Italian girl doesn't know much English. This is a tough one...any guy who pulls it off is generally awarded pimp of the year automatically.
Mac: "Hey Guido, I heard you were trying to pull off the Italian-American challenge last night. Did it work?"
Guido: "No."
Mac: "Ooooh, looks like you got denied on the pimp of the year award again."
by Nick D May 07, 2004
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