An activity to which the person (usually male) proceeds to force a a 5 cent coin down their urethra (dick hole) then wanks and cums with the coin still lodged in there, the challenge is complete when the person has successfully climaxed and then also pulls the coin out.
John: I'm gonna do the 5 cent challenge tonight, wanna do it with me?
Bob: no fucken way cunt, that's fucked
John: it's your loss it's actually quite pleasurable
Bob: whatever you say
Bob: no fucken way cunt, that's fucked
John: it's your loss it's actually quite pleasurable
Bob: whatever you say
by SammySmallDick June 24, 2017

It is a word play of the word duality. It is when a person is being a hypocrite or being two-faced. It can also mean that a person is doing two opposite things at the same time.
Person 1: John is good at doing the Dua Lipa Challenge.
Person 2: He did that sharpener dance Dua did?
Person 1: No, I mean John was being nice to me one moment then he's back to being a bitch.
Person 2: He did that sharpener dance Dua did?
Person 1: No, I mean John was being nice to me one moment then he's back to being a bitch.
by Marcus Ecidius June 7, 2023

The retarded internet virals (other than ikoy-ikoyan/ikoy-ikoy, Rickroll, Sandstorm/Darude - Sandstorm/Sandstorm by Darude, Harlem Shake, butchered languages {anagrams nobody asked for---such as "ngab" or "sabi", "all your base are belong to us", DogE, meme man}, new words nobody asked for {like literally, every Urban Dictionary's definitions}, etc.) which still exists till now
by Sir. B August 31, 2021

The Underboob Pen Challenge is a trend that started in China in late January 2016. It has since then reached all corners of the Internet all around the world. The objective of the challenge is for a female to place a pen, or a similar object under her unsupported breast. It's supposed to prove weather that female is a 'real' woman or not.
Jill: Have you heard of the new "Underboob Pen Challenge?"
Sara: No, what's that?
Jill: It's yet another challenge that sets unrealistic beauty standards on women.
Sara: No, what's that?
Jill: It's yet another challenge that sets unrealistic beauty standards on women.
by Mymojodied May 10, 2016

The art of not masturbating for a period of 14 days (or 2 weeks). It is a tough and grueling challenge only achieved by men with balls.
by Your Handler July 26, 2018

by Gordon Haward October 25, 2017

Ordering a Jimmy John's sandwich with the knowledge of such snappy delivery,"so fast you'll freak," and trying to get your "freak on" before the driver arrives at your door. Set your own personal challenges.
Steve ordered a Gargantuan sandwich from Jimmy John's and rubbed one out, showered, and dressed before the delivery showed up! So fast, he freaked.
Thereby winning the freaky fast challenge.
Thereby winning the freaky fast challenge.
by Buster1234 March 20, 2014
