look up any word, like sparkle pony:
 
1.
can be a sweet heart when its just you and him, but when hes around a bunch of other people he can be a complete asshole. hes charming, sexy, has a nice body, can almost have any girl he wants, amazing at fucking. can be a total bad ass when he wants to be..or at least he thinks he's a bad ass.
krystal:"damn look at that fine ass winston over there!"

jen:"isnt he an asshole to you though?"

krystal:"only when hes around a lot of other people.."
by krissy jem1 May 04, 2010
 
2.
Any being that is filled with win and can perform insta-wins at any given moment.
Jack:Dude what do you think i should say before i die.
John:Respawn in 10 9 8 7 6 5...
Jack:wow your a total winston
by jesus kones January 13, 2009
 
3.
A duck. The most awesome duck known to man-kind.
"Dude, I saw Winston yesterday!"
"Holy Flying Horses! I gotta get that duck's autograph!"
by Vice Pres of Winston fan club January 22, 2010
 
4.
(verb) to ask a ridiculously inappropriate/ blatantly obvious question at the most random time.

or

To make an obvious point when it is totally unnecessary.
Teacher: "Do we have any little questions to raise?"
(To Winston)
Student: "Define...little"

"What type of food does a dog eat?"
(To Winston)
"Dog...now thats a very vague term...define dog"

"shit! we still haven't done freshfields"
by styra November 27, 2009
 
5.
The name given to a small and cute penis!
"What a cute little Winston you have!"
by usmc97 December 18, 2012
 
6.
Every girl has one, he’s the friend there boyfriends hate. Any hint of trouble and he’s there telling her she can do better. With impeccable timing he appears in her hour of need to comfort and support her. The sad thing is she thinks he’s a sweetie and her best friend, he just wants to get into her pants but doesn’t have the guts 2 ask her out.
Lucy: I cant believe he could be so insensitive.

Winston: don’t worry babe, you can do loads better. Tell you what, come over my house and I’ll make you dinner then we can snuggle on the sofa and watch films together.
by winston's girl August 23, 2010
 
7.
The mythical IT/Facilities guy who 'fixes' things that don't need fixing so they *become* broken, or who never appears at all but is always "going to be here next week."
noob drone: "GD it, why don't I have a dial tone this morning? My phone worked yesterday!"

wally-drone: "Dunno. I guess Winston fixed it."

noob drone: "Who the f*k is Winston?? I need my phone to work!"

wally-drone: "He's the phone guy! Just do your best. I think he'll be back next week."
by Willy Codewell July 30, 2012