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Challenge Pissing 

A contest in which the participants try to piss 6 feet straight up in the air without getting wet.
Any way you look at it, Tim, there is only one way to settle this: let's do some challenge pissing.

Challenge Games 

/tsa-lenj gey/

1. (adj.) to be completely consumed by greed, leading to excessively stupid acts like burning bridges, creating crappy products and preventing "sabotage" by deleting "rebellious" information.

2. (verb) to start projects that nobody gives a flying fuck about and ignore those that do matter

3. (noun) a company that used to gain revenue from providing excellent customer service and the ability to play for free, currently in a shitpile due to greed and keeping its players in the dark
1. That company went Challenge Games since they received venture capital.

2. Ugh, no updates today. But they Challenge Gamed some shit on Facebook.

3. Challenge Games <3 Norag Orcs.
Challenge Games by S. Guardian Del October 16, 2009

Challenge Flag

A objection to an improper use of a word for people try to over-extend their vocabulary by faking like they know elaborate words that they do not. (football rules apply for use of a challenge flag and usually a dictionary gets broken out for an impartial ruling.)
Derek: "I did it of my own reconnaissance, John!"

John: I'm going to have to throw the challenge flag on that. I believe the word you were looking for before your down syndrome set in was; "recognizance."

Derek "How dare you unsurp my authority! You shouldn't correct me, I'm your boss. You need to be more pacific about what you're trying to convey"

John : Yeah i'm going to have to throw to more Challenge Flags. It's "usurp" and "specific."

Derek: "Get the hell out of my office, John."

John: "Better yet Derek, lets fight to the death!"

Derek: "agreed."
Challenge Flag by ezekiel2301 February 1, 2010

challenge mode

When someone is doing something and you go up behind them and shake them vigorously while shouting, "CHALLENGE MODE!", causing them to totally screw up what they were doing.

It makes everything so much harder because it's challenge mode.
Katy was doing her homework when David came up and shook her shoulders crazily and shouted, "CHALLENGE MODE!!!!11!1111!!1!!!". Katy's homework was ruined because her pencil went all over the place.

Then Katy pwnd the nubcake.
challenge mode by bullsunshine November 1, 2009

challenge video

Billy: Yo what is this challenge video in Urban Dictionary?
Kevin: What?

Challenge wank 

The act of masturbating to something sexually displeasing, usually over disgusting pornography or someone considerably unattractive. The challenge will be completed if one forces oneself to cum.
1:

"I did a challenge wank over 2 girls 1 cup last night"

2:

Billy: I challenge wanked to Olga's profile picture last night
Sam: No way, that's disgusting! Did you complete the challenge?

Billy: To my disgust, yes!
Challenge wank by shalabon January 6, 2015