"You are going to be stranded on an island. Choose the one item you would bring."
Sounds like the kind of question/challenge Rantings of a Creole Princess* would posit. I came across it when I set up an online account. It's a security question and they ask you to respond with one of the following selections:
So which would you pick?
Would you choose based on what might help you get rescued?
Or what might help you survive?
Or what might make you more comfortable?
Or some other reason entirely?
I could make a pretty good argument for most of these, which I guess is why it makes a decent security question. You have to admit it's a lot more interesting than "Mother's maiden name" and/or "make of first car".
I expect this could also serve as a psychological exam because it probably says a lot about you if you pick one type of answer instead of another. But since it isn't a psychological exam and I don't have a key to pick apart your deep-seated neuroses, you don't need to worry.
Pity the list doesn't include the one thing you'd really need: coconuts. On Gilligan's island, they pulled magic that would have made MacGyver proud**, by making everything out of coconuts. And if their dinky coconut radio could pick up stations, how far from civilization could they really be?
* Great site. JoeBob says "Check it out!"
** If the space-time continuum didn't exist and MacGyver pre-dated or coexisted with Gilligan's Island. Or something.