Sometimes I'll ask someone a question that I think is interesting or insightful, and I get this reply.

I met a UCSB graduate about my age, and I asked him, "How did you ever manage to concentrate, study hard, and graduate from a college with such a gorgeous campus right on the ocean?"

I come from the Midwest, and the college I attended was landlocked and snowy most of the year, so this question seemed like I was stepping outside of my own skin and asking something from his point of view. He started with, "People ask that a lot..."

And in my own mind, I make a mental note: if a particular type of person gets a question all the time, don't ask the next person you encounter matching those criteria that same question. Ask something else.

I try to keep the conversation interesting, not dreadfully predictable.