Has there ever been a time when something told to you or you read made you think hmm? What was it? Why did it make you think hmmm?
Hehe, this reminds me of that Sky One show, brainiac. They had a section with the same title. Anyway, in answer to the question, a lot of things do. History mostly. I always end up thinking about what if things had happen differently, and end up following through an imagined timeline. Very interesting, actually.
Paradoxes. Paradi. Paradoxicals. Wait... um... Anyway, things that "loop back on themself" or are just plain fun to think about. Such as time travel, and if it would work circuitiously or if it would be terminable. (What? I'm confusing myself!) Things that mankind has been pondering from the beginning of time. Like, why do they call them apartments when they're all stuck together? That sort of thing...
When bored in class, I often write down what my top three wishes would be if I was approached by a genie at that moment. (No wishing for more wishes!) It's always interesting to see how my current situation affects my priorities. In fact, reading back on a lot of the things I write at a certain time definitely makes me stop and think, especially because I tend to go over all the memories and things that were happening at that time.
At the moment I'm trying to create my own Universe. ( Not materially, more similar to how Tolkien created his legendarium of Middle Earth and all things beyond. ) Nothing can make you go "hmm" more!
Paradoxes make me go...huh?! Usually pieces of technology make me go hmm. Because I want to understand how they work or why they won't work.