It is always better to be safe then sorry and by being prepared with at least 3 questions you'll be pretty safe. No matter how much you connect with someone on a date there is a potential for the awkward moment or two. So if you are the one that saves the moment with a new exciting topic... you win! Not only do you win the moment for a good save, but most likely another date as well.
Possible Questions:
Job related:
1. What do you love most about your job?
2. What job did you have growing up? Then possibly share a funny story from your awkward DQ or McDonald's days.
3. If money was no object, what would you do for a year? Or with your life?
Movie or Book related:
What was your favorite movie when you were a kid?
What movie completely freaked you out and its probably slightly embarrassing now?
What's the worst book forced upon you to read during school?
Now here are some questions to COMPLETELY avoid, but seem harmless.
1. Will you share an embarrassing moment with me? Why would they? Just so you could turn around and post it as your Facebook status if the date turns out badly. I think not.
2. How's the date going? Now near the end of the date this could be fine if you really are feeling good about this person, but other than that, stay away. If they are blunt then they could crush your enthusiasm and if they are too nice they might lead you into false excitement, but never call you again.
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