Winningest 

An unusual adjective that refers to both the subject and the author simultaneously.

Of the subject: Having the most wins.

Of the author: Being an idiot who can't be bothered to look up a real word.

"Michael Phelps is the winningest athlete in Olympic history"

Winningest by Tom2003 October 14, 2008

winking detroiter 

When a girl tries to deficate on a man as a form of sexual stimulation but can only work up fart in his face instead.

He waited under her with great anticipation but she could only muster a winking Detroiter.

winking detroiter by decoy bot August 28, 2013

Winking Unicorn 

"Winking unicorn" is an expression of a job well done. Whenever someone brings the magic touch to a job or task, that person is completing a "winking unicorn".

Don't worry if you break your broach, just click on your fanny pack and perform a winking unicorn.

Winking Unicorn by Pink Lady 49 January 20, 2015

All out winging it 

When someone does an important project or something they forgot about last minute. This generally involves making it look better than it actually is.

Jason: Dude did you do the project?
Mason: Oh hell im all out winging it.

Jason: good luck getting a B.

All out winging it by thegypsyprince January 24, 2011

Winning Smile Day 

January 21st, the day where everyone if not all will wear the ROBLOX accessory Winning Smile.

Oh hell, tomorrows Winning Smile Day!

Winning Smile Day by Fascist Face December 13, 2020

tri-winning 

awesomeness that transcends beyond even Charlie Sheen's level.

Guy 1: "Charlie Sheen may be bi-winning, but I'm tri-winning!"
Guy 2: "What did you do?"
Guy 1: "I raced a dozen cop cars and won!"
Guy 2: "Thuggin'!"

tri-winning by Da Sperminator June 18, 2011

Winding You Up 

Teasing someone or making fun of them.

It's not true he's just winding you up.

Winding You Up by L.L.Maheswari February 14, 2008