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Challenge shot 

A sexual online game where one player challenges the other to do various tasks. The tasks get naughtier as the game progress. Typically a challenge is to take an erotic picture of one self and send to the other - showing more and more of the body as you go along. However, tasks may also be different - like videos, sound recordings or telling of secrets. Once the person being challenged denies a task, the game is over, so the challenger must try to not go to far.
You next challenge shot is to take a short video of yourself dancing in your underwear outside your house. Do you accept?
Challenge shot by MrLed July 22, 2009
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Challenge run

To beat or finish a video game with a specific task not necessarily required to finish the game in order to unlock achievements or bragging rights. The most common challenge runs are speed runs and no damage runs.
"I just completed the hardest challenge run ever, I beat Super Mario Bros without touching a single coin! I feel like a broke champion!"
Challenge run by jiggysaw17 January 26, 2019

Challenge day love in 

An event that the people that were at challenge day go to that takes place later on the same day or soon after. Where they all get together and hug and kiss each other for several hours and sware there undying love to each other and everyone gets very emotional and which often leads to sex.
Were you at the challenge day love in?

challenge ring

A superficial piece of jewelry worn on the left ring finger indicating an added degree of difficulty in hooking up with her. Similar to a fat friend (challenge cow)
Matt: Dude I really want to fuck this chick.

Kyle: Bring your A game. She's got a challenge ring on.
challenge ring by Matty Ace October 1, 2017

Challenge based service 

Is a uniquely created, social media enhanced, campaign that engages a community of individuals, specifically GEN-Y, and rewards them and their friends for their participation and comments.

Beaconize.me is at the cutting edge of this social revolution.
Beaconize.me is at the cutting edge of this social revolution by designing custom challenge based services.

challenge cow 

The fat friend that always tries to cock block because she's bitter no dudes want to fuck her.
I met the hottest chick at the bar last night but I couldn't close because her challenge cow kept fucking it up.
challenge cow by Matty Ace October 1, 2017

Challenge of the Night

A challenge for when you put a shit ton of red pepper flakes on your pizza to torture yourself and/or impress your friends. Most common with fat asses.