Why do I feel stupid when confronted with questions about Philosophy and yet, I'm strangely attracted to it? Am I a masochist or someone who doesn't know better?
Of course I can't say what's up with you, Victor, since I don't know you, but I can report that the questions in philosophy often have that dual effect on people. On the one hand, they are utterly seductive and mesmerizing. On the other hand, their elusiveness and apparent intractability can be painful at times. Some of the greatest of philosophers have felt the stupidity before philosophical problems that you report; for instance, the Austrian philosopher Ludwig Wittgenstein felt this very strongly and would frequently castigate himself — often before his dumbfounded students — for his stupidity. Perhaps you're right in your suggestion that these traits might be connected: for some people are most attracted by precisely that which remains out of their reach.