Italian-American challenge

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 7, 2004

Penisly challenged

A person with a very small penis.

woa u saw sofia's lil bro when he was coming out of the shower? yeah man hes so Penisly challenged .....
GABRIEL

by Dillon Alexander December 11, 2008

linguistically challenged

Dumb as fuck when it comes to grammar and especially the direction of a question mark

Is my name chas¿ or am I just linguistically challenged?

by Maltido July 14, 2016

PC (phallically-challenged)

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)!

by masseclectic May 17, 2009

Cowan Challenge

Students at Sewanee: The University of the South try to finish a 40 of malt liquor on your drive up the mountain, from the railroad tracks in Cowan to the gates of Sewanee.

I won twice playing the Cowan Challenge, because I'm a little buzzed now

by sewaneehmm April 23, 2007

Sublime Challenger Scat Pack

Because of the limited production of the Sublime Challenger Scat Pack many have not been provided a real life experience of the colors powers. True Mopar aficionados understand that Sublime is unarguably the fastest of all Mopar colors. With not only many years of exclusivity dating back to the 1970's but once sprayed on today's modern muscle Scat Packs they have clearly shown their dominance over all other "regular" hues (including TorRed) and even the other High Impact colors. Sublime has shown its true color dominating both track & street dominance. Long live Sublime's speed superiority! Universally known as the fastest Mopar hue.

The Sublime Challenger Scat Pack is the fastest color of the Mopar hues.

by Dodge Zen February 23, 2019

Round the World Challenge

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

by Pablo Smashitini October 21, 2009