I'm Going to Help You to Become a More Interesting Person
I have a theory which states that everybody is, fundamentally, socially dysfunctional. When it comes down to it, everybody is intimidated in any unorthodox social situation, particularly with people they don't know, and wishes that they could just come out and say something which makes them seem affable, confident and interesting. Although many are shamed to admit it, nobody has anything to say to anybody, really.
Recently, myself and a fellow progressive known as Niall Boyd have begun a crusade to write a social dictionary of sorts - which will basically be a collection of questions and witticisms which can not only break the ice in uncomfortable situations, but completely bypass uncomfortable small talk and place people right in the thick of stimulating, enjoyable conversation. And YOU will hold the biggest presence in the conversation - as you are the one who started it. In an attempt to get ideas flowing for this social dictionary, I have decided to use this blog to, from time to time, offer some of my ideas for questions and witticisms. The revolution begins today.
Why would this question work?
This question is offbeat enough to make it obvious from the start that this is not throwaway smalltalk and that you actually want to discuss this. When people feel like their input is valued - their interaction goes up a notch. Also, the question is interesting enough that, even if someone does answer it in one hit, it will still spawn further conversation.
As there is a good chance that nobody will have an actual straight-up answer to the question, you would need a story attached to it. You will need to comfortable with lying in order to successfully see the conversation through, of course. I actually took the story from an episode of Curb Your Enthusiasm - so I would merely copy Larry David's predicament from that episode if I started this conversation - that being that his acupuncturist sent him orchids and he is unsure whether it is a normal Japanese custom or whether it's some wierd gay thing.
I believe this question would work because, regardless of the response, there should be interest generated. The only risk is that there is next to no response at all - which I think would be an unlikely event.