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1.
A gutsy approach in a given situation. It involves the act of taking a chance where you have nothing to lose; knowing that if you never try, the outcome will forever remain unknown.

Inspired by Wayne Gretzky's famous quote-
"You miss 100% of the shots you never take."

Most commonly used in a situation which involves approaching a member of the opposite sex.
Lucas: C'mon bro, just send her a friend request.
Aaron: Nah man, she'll prob just think im weird.
Lucas: What do you have to lose? Gretzky that shit, man.

Robbie: There's a new job oppening at the Dunkin' Donuts.
Michael: So, why don't you apply?
Robbie: Iuno, I don't think I'm qualified.
Michael: You're being a pussy.
Robbie: You're right. Fuck it, I'm Gretzkying it!
by Matthews Grunfredo January 23, 2011