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Why ask the impossible-to-answer question?

I'll be the first to admit I'm an over-analyzer. I rarely think in black-and-white terms, so even when someone asks me a basic yes or no question, I hesitate before answering, and typically wind up giving an essay in response to the question. Yes, to say I couldn't stand true/false tests in school would be like to say the grass is greener on the other side of the fence, if on that other side of that fence was a marijuana field.

Hypothetical questions, on the other hand, can be interesting. They can provide for some intriguing back-and-forth conversations, which can open people up to a new side of another person. When the hypothetical scenario is more loopy than a Terry Gilliam-meets-David Lynch film, such discussions can be quite entertaining as well.

However, even though I often times find hypothetical questions and discussions interesting, I have a difficult time understanding the impossible-to-answer question when a person presents a hypothetical scenario after the fact.

An example of this would be if a person got hired at Wal-Mart and a few months later was asked the question, "If Target offered you a job before we officially hired you, would you have taken their offer over ours?"

How is the person supposed to answer this question except with, "I don't know."?

He or she was never offered a job by Target, was offered and accepted a job at Wal-Mart, so the questioned scenario never presented itself and never will, since that moment has already passed. It'd be different if the questioner asked the Wal-Mart employee something pertaining to the future, such as, "If Target offered you a job right now, would you take it?" While it may still result in the Wal-Mart employee responding with the words, "I don't know.," the question would actually make sense from a time standpoint, since the possible scenario has not already unfolded, if it will at any point.

Sure, in the first scenario, the Wal-Mart employee could have played along and said something along the lines of, "Oh, no, sir/ma'am, I would never have taken that offer from Target. This is where I'm supposed to be and I couldn't be happier of that!" However, since the scenario has already taken place, the validity of the employee's words could never be proved or disproved.

I was asked such a question just yesterday and felt stuck as a result. My girlfriend joined some family and I at a bar this past weekend to see a band perform. It was her first time at this place. After telling her about my first time there, and being asked by a couple women to dance not five minutes after sitting down (and kindly declining, as they were quite a bit older than myself, I had just sat down, and was talking with my father), she asked me the question, "If we had yet to meet and I asked you to dance, what would you say?"

I kind of chuckled at first, because my first thought was, "How am I supposed to know?" I could have played along and said, "Of course I would have said yes!" However, my brain just doesn't function like that. In the end, I kind of thought, "Why on earth would she ask me a question like that? One that is impossible to answer?"

I wound up giving the only honest answer, which was, "I don't know." Whether I responded with a yes or no, I wouldn't be able to prove either, since the potential scenario long passed us by. 

I think the moral of the story is to never ask an over-analyzer a question which cannot be answered, unless the questioner is prepared for a mixture of silence and words which say little more than "I have no idea" - that or get the over-analyzer high prior to hearing the question.

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