Most Helpful Guy
On a date (especially a first date), can it when it comes to politics, religion, feminism, etc.. and if he is smart he'll do the same. Those come out when you are more comfortable with eachother.
I think its bad to insist that he pay, but don't refuse him if he offers. Conversationally try to be a good listener. It has tons of advantages, like getting him to reveal more about himself than you need to reveal about yourself :) Everyone likes a good listener anyway.
Be yourself and try to be a good conversationalist. If you can have fun, then have it. Guys will like to see you at your best having fun. That will give him more of a sense what you are about.0