Ask crazy stuff it lets them know that you are fun like what's your favorite animal or food or stuff that people don't usually ask start w/ their name first them whatever leads from that!
Who and or what is your GOD, values priorities values beliefs, perceived good qualities in terms of personality and assets(not monetary dummy- touchy area for most men), and what are your limits internal or external? Once you figure out how a guys head is screwed on your can predict his future... The bible says in proverbs : As a man thinketh in his heart , he truly is.
James Allen wrote a whole book about the concept. As I was saying it also is stated in the new testament (corinthians maybe) your thoughts determine your decisions, your repeated choices determine your behavior, your repeated behavior determines your lifestyle and this over time will determine your destiny and future. The hard thing to realize is we are all creatures of habit, the more good habits you indulge in the better influence and outcomes that become possible for your life. This is why I spend a lot of time listening to bible studies because I want as much help at getting the right stuff between my ears as possilbe. Life is too hard, with too many variables you can not control to not want to get as much help making the right choices . Basic Instructions Before Leaving Earth- BIBLE it did not become a world classic without GODS help in writing with 66 authors and 44 books with all the same theme GODS love for man as revealed through the atoning work of Jesus on the cross. Show me what a man thinks I will show you his destiny, Show me how he spends his money I will show you his values and beliefs. Tony Robbins a self help coach indicates that if you need a better quality of answer learn to ask better questions. Learn to qualify and quantify information and never assume you can ask too many questions. I get accused of TMI "too much information" but I can tell you that it is better to have too much than not enough when you get stuck with not knowing what is needed or making difficult choices. The bible is full of wisdom in the book of proverbs. It states that wisdom is found in a multitude of counselors. Don't quit asking, and ask GOD to reveal the aswers if man does not know.
Ask him what job he does, where he lives, what book he is reading or where he is traveling to... Simple and casual everyday stuff. Or better yet, ask him to help you somehow. Guys love to solve concrete and down-to-the-earth problems, and love to lend their hand at helping a lady, using their physical skills. That way he can help you, and you get to know him.
If I was your sister, what could I tell my girlfriends that were curious about getting to know you better? This lets the guy know you respect his requirements for how he likes to be approached and assumes it is coming from a woman in his life he already has a relatioinship of respect with. The problem with men is we all have our peculiarities and huge egos, which can make or break a relationship especially when it comes to sex or intimacy. But thank God that when the right woman learns where and how to push those buttons, it can make all the difference in the world. Sometimes just showing a guy you love and respect those differences between men and women, but are willing to work with them, makes you a keeper RATHER than than a short term fling. When you realize the complexities of relationships you must acknowledge that God must have a great sense of humor!
Just ask him what he likes, what kind of music, movies, etc etc. But don't ask a lot the very first time you talk to him. Just say hey how're you? And let it go from there. Once your talking to someone you'll find it's very easy to carry on a conversation with them.
Wink, smile at him. Then ask what sports you play, what are you looking for in a girl. What food do you like, where do you like going to get clothing.
Make him laugh! Guys love that, at least I do.