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Caroline's eating Ronald Reagan challenge

Thank you brave soldier for fighting the good fight and participating in Caroline's eating Ronald Reagan challenge.
by Sco0by D0o August 13, 2019
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The Guitar Hero Challenge

The Guitar Hero Challenge is doing a girl doggy style while trying to complete a song on expert difficulty.

You can win by either completing the song or cumming while still playing. You automatically get 5 stars for the song if you cum while the song is still on and manage to somehow finish the song.
"Hey, let's bang while playing Guitar Hero. Will call it the Guitar Hero Challenge."
by Milton Wants Sex Bradley March 13, 2009
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Ironman Challenge

A competition amongst the male populace to see who can go the longest without sexual interaction or masturbating during the time of lent. That means no masturbating, handjobs, blowjobs, penetration, or any other form of sexual interactions that could possibly result in orgasms.
"Are you in the ironman challenge?"

"Yeah I've lasted for 5 days already!"
by rsnyper February 11, 2010
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Naked Challenge

Spend the entire day with someone (could be significant other, or just a friend, etc.) butt-ass naked.
(Man 1) "Yeah me and my girlfriend did the naked challenge yesterday... It was pretty cool"
(Man 2) "Dude that's awesome, I've always wanted to do that with my girl."
by jimbob157 March 12, 2012
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Hitler Challenge

Game played on Wikipedia that involves starting on a random page and trying to get to the page on Adolf Hitler by clicking on links in the wiki page.
I was playing the Hitler challenge yesterday, who knew you could get from cheese to Hitler in four clicks
by Wild Ram March 30, 2013
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7 Day Challenge

To abstain from ejaculation for a full week. A true test of manhood, especially among a group of friends. It is unclear if the 7DC is more difficult while being single (masturbation) or in a relationship (intercourse).
Jesse: "What's up dog? Did you know if you don't ejaculate for 7 days your Testosterone levels go up 40 something percent? I tried to do the 7 Day Challenge but I failed. You should try."

Kyle: " Challenge accepted "
by TheRealKon June 29, 2011
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four loko challenge

The four loko challenge is a sacred challenge rumored to never be completed. In order to complete the challenge the contestant must do a series of tasks that could only be described as utterly impossible.

1. The four loko can be any flavor or combination of different flavors, but must be the 23.5 oz can and be 14 % abv
2. You have 4 hours to complete the task.
3. The task must be started at midnight during a full moon and be completed by
4 in the morning.
4. All 4 four lokos must be downed in the first 90 minutes.

5. The next 30 minutes you must win 4 games of beer pong 1v1 meaning no team games.
6. The next 120 minutes can be done in any order but consist of 4 challenges within the challenge.

1. Drive(not ride in but actually drive) at least 4 miles in a vehicle on main roads and stop at 2-4 convenient stores and hold a 4 minute conversation with the clerk.

2. You must call a random phone number and maintain a 4 minute conversation, you only get 4 attempts or you are disqualified.

3. You must chug 4 oz of habanero hot sauce or hotter, no weak buffalo sauce or Louisiana sauce or you are disqualified.

4. Balance on one leg for 4 minutes without the other foot touching.

* The challenge must be witnessed by at least 4 people all recording for 4 hours at 4 different angles with no editing.
My friend died almost finishing the four loko challenge
by Dildoboys March 2, 2019
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