You may want to ask someone what they do in their spare time, and what they like to watch on television as some of your early dating questions. Those are fine, and you should ask them, but they are not as deep as you need to go. You may feel awkward asking more personal questions, but why would you want to be dating someone who has deep fundamental beliefs that are the total opposite of what you believe? In the long run, the relationship is going to fail because neither of you is going to want to change those. You may as well as the right dating questions right off the bat.
Asking the tough dating questions can be daunting, and will make you both uncomfortable at first, but you will be surprised at how well the conversation will flow once the first few are on the table. You should ask about religious beliefs, what they want in a long term relationship, if that is even what they want, and how they see the next five or ten years of their lives going. You may find, through just those simple questions, whether you are both on the right track or if you are opposites with no hope of having anything that lasts and makes you both happy.
You can ask dating questions about the important things like children, job, and philosophies about many important and even controversial subjects. As important as these are, you don’t want to pound someone with them all at once. You have to ask them, but put some fun stuff in there as well. That keeps the conversation relevant and productive, but fun and easy as well. You may have a hard time at first, but it does become easier in the long run. Even if your date twitches, they will find that these are dating questions that they want to ask as well.
