Here's a cute question which Frederic Bourgeois asked me on a train journey recently. He was asked it by Givental, if my memory serves correctly, but I've no idea where it came from originally. Anyway, the question:
There is a mountain of frictionless ice in the shape of a perfect cone with a circular base. A cowboy is at the bottom and he wants to climb the mountain. So, he throws up his lasso which slips neatly over the top of the cone, he pulls it tight and starts to climb. If the mountain is very steep, with a narrow angle at the top, there is no problem; the lasso grips tight and up he goes. On the other hand if the mountain is very flat, with a very shallow angle at the top, the lasso slips off as soon as the cowboy pulls on it. The question is: what is the critical angle at which the cowboy can no longer climb the ice-mountain?
To solve it, you should think like a geometer and not an engineer. (And yes, it needs just one trick which is certainly applicable elsewhere.)
P.S. When I was asked the question, I failed miserably!