Top Definition
You find yourself in a situation in which you must have sexual intercourse with two females separately. The catch is that their collective age must equal 20 years. Thus, if one was 12 years old, the other must be 8 years old. If one was 19 years old, the other must be 1 year old, and so on. What do you do?
Rupert's Paradox has baffled the minds of scholars for years.

"I look to a day when people will not be judged by the color of their skin, but by how they respond to Rupert's Paradox."
-MLK
by Napkin Gladwell September 07, 2011

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