This is a phrase used to critique or make fun of someone who doesn't really know if they like Winston like that. This person feels like they are supposed to pick friend or crush but they cant tell if they even have feelings for Winston. They like flirting with Winston in a romantic way and cant tell if its leading them on or not.
by Dr. Wallaby Jackson March 30, 2022

A Winston is a person that’s nosy and always butting in other people business. A Winston will also insert themselves in a conversation that has nothing to do with them. Note a Winston can be a male or female.
I was in a private conversation with my friend, and a guy walked by and invited himself in our conversation. I said hey can you stop being a Winston. (Side note) A Winston is not a Karen… Karens call the police and are racist.
by anonymous October 21, 2022

Winston is a pussy who thinks he’s rich but it’s mummy and daddy’s boss money so he’s gonna go no where in life and he should stop throwing his weight around if he can’t take to weight that comes with it.
by U want sum fam? August 1, 2020

by Wins.o9 November 29, 2021

by forty2_ July 18, 2025

THe sickest ape to chase your ass. you dash yo ass around, you look behind and you see a big banana head with a tesla ready to torch your ass
" Bruh, that donkey winston just killed me.
" Bruh, that donkey winston just killed me.
by Football vibes October 11, 2022

by Esileandeiddam January 19, 2019
