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."
Guido: "No."
Mac: "Ooooh, looks like you got denied on the pimp of the year award again."
by Nick D May 07, 2004
Where one pokes another individual in the bum hole region without them knowing you are there,whilst screaming "bum hole challenge" at them!
Jack poked sally in the bum hole whilst she was washing up and shouted "bum hole challenge" very loud, scaring the shit out sally!
by Sinner15 December 28, 2013
The task of shagging a girl from as many different countries as possible, ideally all of them! 1 point for 1 country, doing them in their own country counts as 2 points, 3 points if they don't speak the same language. Paying for it doesn't count
I had an awesome summer backpacking, I managed to cross all of Europe off the Round the World Challenge.
North America is the easiest place on the Round the World Challenge, next on my list is South America
North America is the easiest place on the Round the World Challenge, next on my list is South America
by Pablo Smashitini October 21, 2009
When a man has a small penis
Gretchen: "How was your date last night?"
Paris: "So PC, I won't be going out with him again."
Gretchen: "You are such a liberal! I can't believe you met a guy who is more PC than you."
Paris: "Not politically-correct! PC (PHALLICALLY-CHALLENGED)!
Paris: "So PC, I won't be going out with him again."
Gretchen: "You are such a liberal! I can't believe you met a guy who is more PC than you."
Paris: "Not politically-correct! PC (PHALLICALLY-CHALLENGED)!
by masseclectic May 18, 2009
by Ronin 007 February 13, 2014
Some dumb ass thing we had an assembly about because a dumb ass bitch told somebody to kill themselves and told the bitchy VP that it was a challenge
by HarleyQuinnBitches December 13, 2016
The premise is simple but the task difficult to achieve. The goal is to not masturbate for a full 3 months, or 90 days. When completing the 90 day challenge one must not masturbate at all within 90 days. If the participant masturbates (even without achieving orgasm) he or she is allowed to restart the next day.
by Groggiepai September 12, 2010