Small Talk: the Death of Conversation

Several weeks ago I went on a hike with some geology people. One of them is a Muslim boy from Indonesia. When we were driving back I asked him what was the most surprising/confusing thing about this new culture he was currently immersed in. His answer floored me, although I agreed whole-heartedly. He said that he hated how conversations all started with "How are you?" here because that was usually where they ended too. He talked about how impossible it felt to actually get to know people because the small talk killed all chance for connections (well that was my interpretation). He said in Indonesia people often invited each other to go places together to get to know them which was more effective.
Around the same time I moved into a new apartment and found myself at several social events (including church... not always a social event but for what I am talking about here for all intents and purposes it is). I felt like every new conversation was identical to the last. "What's your name?" "Where are you from?" "What are you studying?" "How far along are you in your degree?"
Notice how none of those questions have "Why" at the beginning (I am convinced most conversations get interesting when why is asked).
I kind of just wanted to give up, I mean why bother talking to people when the conversation is so redundant I won't even remember who they are or what we talked about 10 minutes later?
At another activity I decided to try harder and I asked a girl what the most boring thing she did that day was. It was a far more interesting conversation.
I decided I really wanted to ask questions like this more often, throw out the boring questions I mentioned already, but there are two things I didn't like about that question. 1) It is a "favorite" question, and sometimes asking a "favorite" or "most" question is annoying because it puts undue pressure on speaking accurately... I have to think too long about it and that is not really necessary. 2) It focused on a negative aspect of life... I don't want to ask for complaints.
So then I spent some time trying to think up questions that I could ask that weren't boring. Here are a few I thought of:
What was the last animal you saw?
Do you like trees or mountains better?
What inanimate object makes you smile?
What made you smile today?
I asked the trees or mountains question to someone and they said "Why?" which I guess is the epitome of the problem.... non standard questions aren't really seen as quite acceptable, and thus, I often don't have the guts to ask them.... and then I dread asking the boring questions I just don't ask anything...
So is the compromise just asking the boring questions with "why" follow up questions (that works ok sometimes)? Or just to stop caring if people are totally confused when I ask them about odd things?
Of course I could always just stop talking to people I don't already know. I just can't get over how an outsider who had such a different culture background focused on how westerners kill the possibility of relationships before they even begin all with our small talk. Let's stop sabotaging ourselves!