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During Charlie Sheen's "reinvention" of himself as a tiger-blood-dripping warlock, one of his favorite mantras is "WINNING!" This particular usage is most common on Twitter, where the pound symbol (#) indicates a trending topic to follow.
Face it folks, you just feel better when you say it. #WINNING

#WINNING! #teamsheen

RT @ParisHilton @CharlieSheen Hey Neighbor, I think I might have #Tigerblood ;) and I'm definitely #Winning! Can't wait for #Sheen's-Korner
#WINNING by jimmyjohnbrown March 26, 2011
An adjective for somone who surpasses the definition of Winning, therefore # is placed before the word.
Charlie Sheen is #Winning
#Winning by #Winnanator March 25, 2011
wearing the same clothing as your friend
OMG we are wearing the same vans #twinning (now you usually take a photo)
#twinning by itswhatervrs November 3, 2013
Charlie Sheen + #WINNING-
bang 7 gram rocks = # WINNING!

pints of tigers blood = # WINNING!
# WINNING by brokenglass420 March 29, 2011

#WinningOnPurpose

Having a attitude that you will accomplish, achieve, elevate!
I passed my math test today. #WinningOnPurpose. Yes!

No matter what comes my way. I'm going to have a #WinningOnPurpose Attitude!
More from Urban Dictionary

kinktober 

An excuse for people to write porn with different types of kinks throughout the month of October.

Smut Fanfiction
That chick doesn't write often but when she does, its for Kinktober.
kinktober by Kinkiest July 12, 2018
Word of the Day on October 30, 2026

proper lad 

a lad that is such a lad that he is a proper lad
person1:did you see bob
person2: ya he was a proper lad
Word of the Day on October 29, 2026
The number of years you are still sexually active
While our lifespan is the number of years we will live, our healthspan is the number of healthy years we will have and our sexspan is is the number of years we will continue to be healthy enough to continue having an active sex life.
sexspan by Dr Kat April 21, 2022
Word of the Day on October 28, 2026
A lighthearted reaction upon receiving disappointing news of some sort. Usually something that isn't a particularly a big deal, esp. when it primarily affects someone else - sort of a mild schadenfreude. Sometimes doubled or tripled, and possibly said in a sing-songy voice for added comedic effect to imitate a muted trumpet, which is how the meme originated.
You didn't get any napkins with your takeout pork fried rice? Womp womp.
womp by 175623226 November 3, 2011
Word of the Day on October 27, 2026
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