So, what makes for a great question, as opposed to a dull back-and-forth? More important than the specifics of the question is your intention in asking it.
If you don't truly care about the answer, then any question will fall flat. Avoiding yes or no questions creates organic conversation, and allows you and your date to really get to know each other.
It also opens up new avenues of communication based on that positive information.
seem to want to talk about work, this is a great follow up question.
And it guarantees that her response will be more than a one-word answer.
If she doesn't like her job enough to include it as part of the week's "best of,” then you’ve avoided that landmine.
And lastly, your questions should blend into conversation naturally, building on the most positive points.
It's better to save a common topic for later than remind her of a place she doesn't associate with positive feelings.
Remember, a first date should be fun and pleasant—an enjoyable distraction from her everyday routine.
Look for the deeper information contained in her responses.
Travel is a great shortcut to deeper values and priorities.