By asking her to talk about the not-so-fun parts about dating, you're not trying to get her to vent, but to lightheartedly acknowledge that dating can be awkward.
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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.
The places she has traveled as well as the places she wants to travel give you a lot of insight into who she is.
A girl who wants to hike Kilimanjaro has very different interests than a girl who wants to stay in every seven-star hotel in the world.
How she spends her professional life will tell you how she feels about money, colleagues, the workplace, and her time.