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Dating questions 101

Regardless of whether you are in the online flirtation mode, speed dating, or on a real live date, asking questions is the best way to get to know someone and determine if you want to pursue future contact. Don’t be “Minnesota nice” asking only simple easy to answer questions.
The primary reason for asking questions of a potential love interest is to get information, so that you can get to know them better. Throw out all the questions that allow for “yes” or “no” answers, and learn to formulate your questions such that the answer will be something containing information.
For example, if skiing is a big part of your winter activities, you’ll want to know if this person skis. Don’t ask, “Do you ski?” Instead ask, “If you could plan a ski trip anywhere in the world, where would it be?” Ask a follow-up question when you get an answer. The answer might be “I don’t ski, so I don’t know where I’d go.” Then your response might be “What types of outdoor activities do you enjoy?” Or, maybe the answer was something along the lines of “I’d plan a skiing trip to the Swedish alps.” Your follow-up question can then be a simple “Why?”
Remember that this interview is a two-way street and you are hoping for mutual results. If skiing isn’t their cup of tea, but they do enjoy skating, you’ll need to determine whether this matters to you. If it does, you may want to go on and on about how much you love to ski and that you spend most of the winter doing just that. If they’re listening they may take this as a signal that you may not be the most compatible pair after all. However, maybe it is just important to you that they enjoy being outdoors in Minnesota in the winter. If so, then you may want to pounce on the subject of skating and learn more about where they go to skate and how often.
It really doesn’t matter if the subject is skiing and skating, or reading and watching TV, or eating meat vs. vegetables. It is all about getting to know the other person and not falling into the roll of an interrogator firing a barrage of yes/no questions that have no depth to them.
Are you still at a loss as to what kinds of questions to ask? They don’t have to be super serious; they can be fun and inventive.  Here are a few examples:            
  •        If your best friend was going to tell me three things about you, what would they be?
  •         What's your favorite airport in the world?
  •        What countries have you visited?
  •         Do you listen to your own music or to the radio?
  •        If you won $100 million in the lottery, how would you spend the money?
  •        If you were an animal what animal would you be? Why?
Use your imagination, and don’t let the answer to one question make your decision, unless it is a really important one like “Are you married?” And the answer is “Yes.”

Don't ask "yes/no" questions
For more info: 

   On 45 speed dating questions

  About skiing in Minnesota