Seeing if you are compatible with someone is much harder than one would originally think. If you are an amicable enough person, getting along with people can be easy enough. You might get along with someone great but could never have a successful relationship with them.
Honestly, life is too short to be too scared to ask the hard questions. If you want to be dating this person, you should want to just dive right in, and get to know them. Some of these may seem like premature questions, and that you're concerned with scaring the person away—but I believe that if you are dating someone you should see a future with them, and why waste both of your guys' time if you aren't even on the same page?
This is something I have personally learned over the years since I am a pretty confrontational person. I will just go right in and ask someone a relatively intimate question, and if that person is uncomfortable, then right there I know we're probably not a good match. Even though everyone is different, communication is still very key in every relationship. Don't be afraid to ask some of the hard questions at the beginning of the relationship. If anything it will bring you both closer, or show you right off the bat that maybe you're not the best match.
Here are 30 of the best questions to ask on a date: