My vote for the worst question ever:  "What's new?"  How am I supposed to answer that question?  Do people really want to know the answer?  If so, how long of an answer do they want?  Five minutes?  Five seconds?  How specific should I be?  If I bought something used, does it count as being new?  Doesn't it depend on how long it's been since I've seen the person?  If I haven't seen the person in 10 years, where the heck should I start?  How inclusive should I be?  Should I mention the new white undershirts I just got from Walmart?  Or is that not important enough?  Should I say that I got my car washed the other day?  Technically, it's new ... in a sense.  Should I talk about the new emails I got today?  They're new.  Does that count?  Or should I look at the really big picture and say something along the lines of, "My interest in theoretical physics has subsided mildly as a result of my new-found love for conveyor-based plane takeoffs"? 

I guess I understand the point of the question:  "How do I get this socially inept introvert to tell me something interesting about his life?"  But I'm so unsure of how to answer it that I almost always just end up saying, "Not much."