Women love to talk (just think of how long they talk on the telephone). Women like to help (just think of a typical “female” job: nurse, kindergarten teacher, geriatric nurse…). Combine those attributes and you got a talk up and running by asking the woman: “Could I ask you for help? Could you tell me why/what/how/…”. Ask her any question you like as long as the question is non-answerable by a simple “Yes” or “No”.
Believe it or not, but maybe you have failed in your last dating attempt because you maneuvered yourself into dead-end answers. If you ask a girl “Have you been long here?” then practically anything she can answer is a dead end. She could answer “No, not long” or “A couple of minutes” but both answers do not lead into a nice conversational flow.
Many men (since men are practical-minded) want a “clear and simple” answer. For dating purposes that kind of “questioning strategy” is absolutely wrong.
Train by simply re-phrasing some of your question. Wrong: “Do you like this place?”, right: “What do you think about this place?”. You get the idea. In other words: Let her TALK. (This is just a simple example and I am not telling you to ask women that question).
Or ask her something like: “What do you think is the most common flaw men have?” or “I am writing for dating-forum.com. Could you help me by telling me what feature your ideal man should have?”. Let her talk for hours.
Typical “open questions” start with
You get the idea.