Rupert's Paradox 

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

Rupert's Paradox by Napkin Gladwell September 8, 2011

Rupert's Dementia (RD) 

A form of long-term delusion resulting from watching too much Fox News.

Timmy was showing signs of Rupert's Dementia (RD) when he accused president Obama of being "just like Hitler."

Rupert's Dementia (RD) by jimbo92107 May 23, 2015

Rupert's fingers 

Rupert's fingers is the local name in England for a hot dog, or more occasionally a Vienna sausage.

Hey man you want some "Rupert's fingers"?
Chill and have a "Rupert's finger".

Rupert's fingers by cannnibal of fish April 27, 2022

Prince-Rupert’s-drop

The aftermath of jacking off on the toilet and wiping it clean, but, sitting there long enough the extra discharge dripping out when you stand up creating a prince -uperts-drop dangling 2-4”and eventually falling into the water.

The prince-Rupert’s-drop would not detach from his penis.

Prince-Rupert’s-drop by Panch above the rest January 5, 2023

Rupert Syndrome

A disease that causes immense neck pains, and an obsession for knee guards, being infected makes the ill person want to express their pains and obessions.

The sick patient had Rupert Syndrome and could not stop talking about neck hurts and knee guards

Rupert Syndrome by gonna_eatpizza May 8, 2026

Sir Rupert the Bear 

A perverted bear like creature that lurks in UK.Very dangerous when horny has a an affection to Margaret Thatcher and Angela Merkel who fancies as the ultimate dominatrix.

Oh Shit is Sir Rupert the Bear hide your daughters.

Sir Rupert the Bear by asid72 January 9, 2012

Stupid Rupert

Khalid Allen is a Stupid Rupert. And he is a bum.

Shut up ya Stupid Rupert-Jeff Solomon

Stupid Rupert by Bob Frankenlin December 28, 2007