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3.
It's like The Game except you win when you think about it.
Bob: I just lost the game.
Jill: Oh man, I lost the game. But I won the challenge.
by GameChallenger April 11, 2010
 
1.
A variation of "the game" in which the point is NOT to remind people of the challenge, because if you remind someone of the challenge, they are allowed to punch you once in the arm.
the rules of the Challenge are as follow:
1) you can only punch the person who reminded you of the challenge in the arm, no one else
2) if someone directly refers to the challenge, and it reminds you, you may punch that person twice
3) you only have to tell the person you punch that they reminded you of the challenge, unlike "the game" where you have to admit it out loud
4) if you remember the challenge without being reminded, you must punch a wall
5) after being reminded of the challenge you have a one hour grace period in which you cannot be reminded of the challenge, you may not punch people as part of the challenge during this time.
etiquette:
please apologize for punching someone after you do, then explain to them it was because of the challenge.
guy 1: ninja gaiden 2 is so challenging

guy 2 punches guy 1

guy 2:sorry, you reminded me of the challenge
by Ian Marvin :: Jacob Denver February 03, 2009
 
2.
The Challenge is the 40 day period of Lent when a man cannot masturbate. The Challenge is a long and gruesome waiting period. Not many men can hold out.
"hey man, how far did you get in the challenge last year?"

"30 seconds, what about you?"
by thechallengewascompleted February 13, 2013
 
4.
The challenge is the set period of time at cadet camp where you do not masturbate. The only way to WIN the challenge is to have intercourse. Basic cadets usually masturbate in secrecy in fear of receiving a red chit for self mutilation.
Sgt. funk: "Hey man, hows the challenge going"?
Mcpl: "I failed two weeks in".
by Mr.definition March 05, 2014
 
5.
The ultimate competition of all time, where true legends are born. This is how it goes down: teams of four race to take down a 30 rack, smoke an 1/8 of weed, eat a large pizza, and then complete a 100-500 piece puzzle. If a team member pukes, he or she is forced to sit out for the remainder of the game
Sean: Hey, Sam's house is open this weekend, you down for The Challenge?
Joey: Hell yeah, its game on.

Steve's team struggled in the final round because Ron drunkenly ate one of the puzzle pieces during The Challenge
by CBN1 June 25, 2011