The pool is a planet and the man is a room outside
"the pool is a planet and the man is a room outside" was an "answer" to a notorious riddle by Absurd Questions that appeared on Current Events on April 28th, 2008. It reached fame and became a meme on CE.
The original riddle was this: "A man has to get across a pool full of sharks. The sharks are hungry and he's delicious. However, the bloke is able to cross from one side to the other unscathed. How does he do it?"
After around 150 posts of various theories, the topic creator, Absurd Questions, gave the solution. This caused far more confusion than even the original riddle did, though Absurd Questions insisted that understanding it only required some lateral thinking. He went on to explain that his riddle was an old traditional Macedonian riddle, which meant about as much as the answer did in terms of actually explaining how the riddle was supposed to work.
While the whole thing was almost definitely a troll topic, its pure absurdity, in addition to Current Events' response which had sprung the topic to 500, gave it a legendary status as the king of stupid questions/answers. "the pool is a planet and the man is a room outside" is still referenced occasionally whenever a nonsensical question is posed on CE.
TC: Dean's father Derek passed away, and in the will he specified that if Dean guesses the password for his... [tl;dr] User1: the will is a planet and Dean is a room outside