
You want to discover something about who this unknown woman actually is and not just who she wants you to think she is. It would be nice if women wore labels like "Gold Digger" or "Daddy’s girl" but they don’t. So it is up to you to find these things out and you can’t merely ask direct questions. You need to know what mistakes you will be able to keep off and how to impress this lady if you decide you want to do that.
As soon as you are past the initial small talk, ask her, "What are the biggest mistakes guys make when dating online?". Listen cautiously to her answers. She is going to tell you several things about herself and her positions on men in general.
Next you should ask her, "What do you actually think about online dating?". Now she will tell you if she has had any bad experiences dating online and assist you to keep off making the same things wrong.
And now for the essential one. "What caused the break up in your last relationship?". If she puts all the fault on the guy, you should probably pass on to the next candidate. If she takes all the fault herself, you should probably do the same. If she states the breakup was by mutual consent or that the relationship just was not proper for either of them, you have heard the right answer. Go ahead but always with caution.
Asking the proper questions will give you insight and make you more convinced when you meet the lady for the first time.