How could one go about stumping the Stovohobo? Is it possible, is it right?

I could ask him of physics and calculus, but that is too easy and it would be rather simple to just google it.

Now to win this contest I could ask him of fencing, a subject I know very well, but will Stovohobo rise to the challenge and declare victory with his awesomeness fortitude of mind?

Perhaps a question about something obscure, like the good ‘ol question that goes something like this, “If a tree falls in the forest…” Ah, no too cliche.

Well then that leaves only one possibility, ask the question that has no answer, but in that it has no answer it reveals many solutions. Bring my question to the unanswerable, which is inevitably solvable. So, now for the greatest question ever...

If a train leaves Philadelphia at 2:00pm going 69 miles per hour and a train leaves Charleston at 1:30pm going 53 miles per hour what is the probability that both train conductors will have blue eyes.