Paradoxes & Riddles


As an undergraduate about to enter law school, Bailey Winepol put into action what he thought was the perfect scheme to avoid paying school fees. He managed to persuade Lock Haven Law School to sign up for a deal that would contractually oblige him to pay double the normal school fees, but only when he won his first court case. Until then, he would be required to pay nothing. However, what the administration at the law school did not know was that young Bailey only ever intended to take on cases that he could not possibly win.

Sure enough, this is precisely how his career has unfolded in the five years since he was called to the Bar. Winepol has built up a successful business by means of the shrewd application of the following guiding philosophy: strive to take on only those clients who have committed their crimes on national television and then signed a confession in front of millions of people.

Unfortunately for Winepol, a new face has recently taken over the reins of Lock Haven Law School, a Professor Protagoras, who is not prepared to tolerate these shenanigans any longer. The professor has come with a plan every bit as devious as Winepol’s in order to get him to cough up the money. He decides to sue Winepol in court for the money he owes. Protagoras doesn’t expect the law school to win the case, but he believes that it will end up getting its money anyway. He reasons as follows: if Winepol wins, then he will have won his first case, which means that he will be obliged to pay the amount he owes. If he doesn’t win, then it means that the court has confirmed that he has to pay the money. Either way, Lock Haven Law School gets  paid.

Winepol, needless to say, doesn’t see it quite like this. He believes that if he wins the case, it means the court has determined that he doesn’t have to pay the money. If he loses, he has still not won his first case, which means that he is not obliged to pay. So either way, the law school does not get paid.

Which of the two of them has got it right? And why?



DoorsYou are in front of two doors; behind one is a ferocious lion, behind the other door, a pot of gold. The doors are watched over by two guards. You are allowed to ask just one question. One guard always tells the truth. The other guard always lies.

What should you ask in order to determine which door the pot of gold lies behind?


Brighton Commuters look away now – this riddle may be upsetting.

TrainTrains travel from London to Southampton all through the day, always on the same track, always going non-stop, and at the same speed. The two AM trains took eighty minutes to complete the trip, but the four PM trains took an hour and twenty minutes.



 SwanThere are two swans

in front of a swan,

two swans behind a swan,

and one swan in the middle.

How many swans are there?


LiftA man lives on the thirteenth floor in a block of flats. Every weekday he takes the lift to go down to the ground floor to go to work. When he returns, he takes the lift to the eighth floor and then walks up the stairs to reach his flat on the thirteenth floor. If it is raining, he does the same thing, except he takes the lift to the tenth floor before walking.

He hates walking, so why does he do it?




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