Open ended questions: Question #1: What were you like in high school?
You might want to follow up with “Were you the popular cheerleader type, or the nerdy chess club kind of girl?”
Funnily enough, MOST girls are going to say they’re normal (ie. somewhere in the middle), even if they were in one of these extremes.
This can naturally lead into her talking about her journey to become the woman she is today.
2: : What’s it like dating guys in your city?
By far my favorite question.
It’s quite a “revealing” one as every woman has strong feelings attached to it.
So by asking this she’s going to feel like she’s known you for years and also creates this “us vs. the world” dynamic.
And I also like to follow up with “What’s your worst dating horror story?”
A fun and playful conversation ALWAYS comes out of it.
you can tease and say damn you used to lame boring guys, i might be too exciting for you etc
change these to suit your own persona
3: If you could go back in time and give your 12-year-old self advice, what would you tell her?
Also reveals a lot about her dreams, desires, and regrets. You can even use this to discover red flags.
4: If you could choose any character from a movie/anime/book, what would that be?
5:Let's say you are going to become really close friends with somebody. What are two things you want them to know about you?
Please add your own and contribute to all of them especially qualifiers and disqualifiers
which i believe the most interesting questions help you become most interesting in her eyes and make her chase