So I'm witness to a lot of first dates and I hear a lot of 'getting to know you' type questions.
Dating seems a lot like interviewing for a job.
I used to do the hiring and interviewing for a company I worked for and asking the same interview questions over and over again just became extremely tedious. People would come in and be so nervous - they would have their set, prepared responses to the standard interview questions; 'What are your strengths', 'What are your weaknesses', 'Tell me about a challenge at work you've overcome'...whatever.
You could see them not really looking at you, just kind of trying to get out this memorized statement. So every now and then we would throw in some totally random question. 'What's your favorite monty python skit?', 'Who's your favorite superhero?'. 'Tell me what you would do if you won the lottery'. Some people that were working off their memorized lists would be totally thrown for a loop and not really know what to say. Others would loosen up and start to have some fun with the interview. Those would be the people we would hire.
I tried speed dating a couple years ago (that thing were you rotate around a room and spend 5 minutes with about 12 different women over the course of the evening) and it was very much the same thing. I'd get the same questions from a lot of the women, the old 'what do you do for a living', 'what do you do in your spare time' - nothing particularly creative. So I would start throwing in a couple weirder questions just to change things up a bit.
Needless to say - I left alone and wasn't long for the speed dating thing (although the girl organizing the evening did ask me out, but that's another story)
So what's the weirdest question you've ever been asked on a date?