The first date is your best chance to make a good impression. Please don't mess up a potential new relationship by asking any of these awkward questions too soon.
1) Anything about his ex.
This is a big NO-NO! Do not mention/ask anything about his ex partner. This is your time to get to know your date instead of interrogating him about his past.
2) "Do you watch porn?"
Unless you want to come across as a total weirdo or a complete freak, keep this question to yourself.
3) "How many women have you been with?"
This is an extremely personal question that is completely irrelevant when you are first getting to know someone. As curious as you may be, some things are better left unsaid.
4) "How much money do you make?"
Instead of asking such a personal question, perhaps ask about what he does for a living or his career plans. This will not only help the conversation flow, but also give you an idea of where he stands financially.
5) "Do you want to get married?"
While you may think this is a harmless question, it can seriously scare off your date! Save this question for down the road if you actually start dating.
6) "Have you ever had an STD?"
Unless you want to jump into bed with him right after your date, don't ask until you are ready to take that step!
7) "Do you think I am pretty?"
If he didn't find you attractive, he wouldn't have asked you out. Asking a question like this shows a lack of confidence.