Asking your date what his five-year plan is may be a bit much for a first date, but you can still find out what he hopes to do or have in life. Ask about his career goals. If you feel comfortable asking about what your date wants in his personal life, ask about his views on children and marriage. Be careful with these questions and your own responses so that it does not seem like you are desperate or putting pressure on your date.
Likes and Dislikes
You need to know whether your date (and potential relationship partner) is going to expect you to see every romantic comedy that ever comes out, despite your yowling protests, so being aware of some of her likes and dislikes from the beginning is important. Be careful not to shoot out question after question interview-style. But finding out what your date likes to do on the weekends or on vacation can be very revealing and can help you decide how compatible you two may be. Favorite foods, books, and architectural styles are all fair game, but you should probably avoid questions about her preferred toilet paper or laundry detergent.
Views on Important Issues
Politics, social issues, economic and financial values are important issues that must be discussed in any relationship. Whether the two of you agree upon issues is not the most important thing from the beginning, but you should be able to discuss the issues without ending up at one another's throats. So, asking about your date's views on an upcoming election, a volatile current event or the inflation of the price of gold can keep conversation moving and help you decide whether another date is in the future. You should make sure also before you discuss any current event that you are well abreast of the situation.