The answer should reflect his plans for the next 3 years.
What are your long term goals?
The answer should reflect his plans past 5 years and should not contain the any of the answers from the first question.
What is his relationship with his family?
You should pay attention to his relationship with his mother. A guy’s first female relationship is with his mother, if he does not respect his mom or have a good relationship with her, you might want to end the question asking at that point.
Questions to ask before having sex ask but not on the first date
What does he think about you? & What does he feel about you?
It’s important to note that his answers to these questions should not be the same. Mean think and feel differently. If his answers are the same, it may be time to move on.