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Fly the basket is a slang term for Flat Out Ask Him.

When ever you have something important to ask someone and are embarrassed to ask them all you need to do is fly the basket. The term can be used in code whenever you are around the person a question needs to be asked of.
"I wonder what Dane thinks about Blake..."
"You should just fly the basket"
"Look, here he comes! Now is your chance, Fly the Basket!"
by TSMGOKBK February 21, 2011