Challenge 

One of the two roles men can play in picking up girls. A challenge is a guy who plays hard to get. He says things like "Do I have to call you?" or "Im not sure if i should be with you". Although for some guys it is hard to do and may feel awkward, it is the best way for picking up girls.

The Challenge is the opposite of the Wimp, which is the guy who calls on the first night and says "I Love You" after the first date. Basically, the Wimp is the guy who will be pussy whipped

"Bro, i told that girl i didn't want her number but I got it anyways. Being a Challenge has really helped me pick up girls easier."

Challenge by Sean47 September 10, 2007

challenge 

a drinking game orgininated in the northeastern oregon town of milton-freewater. at any moment during a party if you've heard the word "challenge" shouted you must consume whatever you have in your hand as fast as possible. this is a good way to weed out the pussy drinkers who think they're rugged.

assists are also allowed

challenge: straight up

guy 1: dude that chick over there is hot.
guy 2: you should go over there and CHALLENGE!

challenge: with assist

guy 1: hey chuck, fill in the blank. i _______ you to a dual.
guy 2: is it by any chance, CHALLENGE!

challenge by dylan w April 16, 2008

Challenge 

a call to someone to participate in a competitive situation or fight to decide who is superior in terms of ability or strength.

They challenge you because they see the way you treat me .

Challenge by ... Zjdbckdnznsjd December 1, 2019

Challenge 

No, actually. I didn't say that but I'm glad you brought that up because it perfectly reflects what is happening here.

Hym "I said there is no challenge. You are trying to be the challenge but instead you're a moron. You're not actually engaging with the things I say. You are trying to pretend kill all men and men are stupid and useless or that you didn't use small dick as an insult as though time started the second I started writing. You want to pretend THAT didn't happen for years in the same way you're trying Kendra wasn't fucking that retard or that I didn't create AI. I'm not pretending with you. I'll kill your fucking kids if I don't get the credit and that money and retire immediately."

Challenge by Hym Iam June 5, 2025

challenge pissing 

A challenge where you try to piss six feet in the air straight up and not get wet.

Hey bill, you want to do some challenge pissing? I guarantee I'll win

challenge pissing by Shark Attack April 12, 2007

Challenge pissing 

A contest held at Big Bill Hell’s car dealership in which the contestant is challenged to piss six feet straight up in the air and avoid getting wet. If they’re dry, they receive no down payment on their car

“Take a hike to Big Bill Hell’s, home of challenge pissing!”

Challenge pissing by JustAVitalVestigialOrganHere November 8, 2018

Challenge pissing 

If you can piss 6 feet straight up in the air without getting wet, you win.

Challenge pissing would be easier in space.

Challenge pissing by unstoppable idiot January 12, 2009