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award winning 

This term is used to connote positivity, or negativity with a particular situation, or object.

On its own, the term is good. But, mix up your words a bit, and you can flip it around to make it seem bad.
"Dude I crashed into a manure truck the other day."
"I'm not surprised, your driving isn't exactly award winning."

"That Klipspringer is an award winning son of a bitch."

"Dude, Terry is so rico suave with the ladies, it's award winning."
award winning by Raney November 19, 2004
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Bi Winning

The art of always winning weather your filiming two and a half men or slamming 7 gram rocks.
Liz and Dustin are bi winning

The Winking Skeever 

When you tickle one's butthole with a winking motion of your eyelash, while giving them a reach-around.'

ALSO

A bar inside the Elder Scrolls V: Skyrim game.
That skanky bitch just gave me the winking skeever last night, but the joke is on her cause now she has pink eye.

That whore took such a close look at my balloon knot, she damn near gave me a winking skeever.

{Skyrim} My character went into The Winking Skeever, paid a septim, and recieved the winking skeever and now has learned a new shout!

A winning streak 

Lou Brown: We won a game yesterday, if we win one today that's two in a row. If we win one tomorrow that's called a winning streak. It has happened before. SO LET'S JACK IT UP A LITTLE!

Near-winning addiction 

Excessive gambling habit indulged by grannies who keep buying lotto tickets and scratch cards thinking that near misses indicate a close big win.
Grandma is always broke. Any money you give her feeds her
near-winning addiction.

Bi Winning

1.Winning over here, AND over there.

2. Opposite of bipolar
Interviewer: Are you Bipolar?

Charlie: Bipolar? Whats that? Im not bipolar, im bi winning.
Bi Winning by FranciscoTheRobot March 20, 2011
1. I'm just winging it.
2. I was totally winging that.
Winging by Ninja Shirley June 22, 2011