A Limbaugh Dilemma is the term referring to whether or not you should ask for a really expensive item and risk looking like an ass, or hope that you get offered a moderately expensive prize, but risk getting offered nothing at the same time.
On the Rush Limbaugh show, a caller asked for a MacBook, only to be told that he was going to be offered an iPad had he not said anything. This establishes the basis for the scientific term known as the "Limbaugh Dilemma."
by MacBookGuy February 22, 2012