The first day you go out on a date should be a day that you get as much information on him as possible. It does not need to be like you are interrogating him, but let him feel ease and share as much as possible so that any doubt will be removed.
Ask him these questions which will help you understand him better:
1. What do you do for a living?
That should be the first question. Unless you want to date a serial killer, who kills women in apartments and robs their money. Even if he lies to you, you will find out eventually. Sometimes he might not expect this question, but the following questions will reveal his real character.
2. How close are you to your family, when did you last see them?
This will help you understand what his family is like, where they live and how he relates to them. How he relates to his family will greatly influence your relationship
3. Ask him whom his role model is
This will expose his passion, values and his vision to you. Finding his role model will be like finding him too. Why he likes that person also will.
And the last question:
4. What do you want in this relationship? Casual dating or long-term?
This will help you know whether you are on the same page with him. This will avoid having any misconceptions when you argue about something.