Ask a guy questions before dating
If you are allowed to do just one thing for the rest of your life, what would it be? What are some things about you that you take pride in? What is the most courageous thing you have ever done in your life? Will you be OK with me hanging out with you and your friends? If you could change something about your life, what would it be? Again, when that point is will depend on you and what you think the other person is ready to respond to. You may consider making a list and have them answer the ones they are able to answer.
What’s your biggest regret that you have in your life so far?
Can you have emotional intimacy without physical intimacy?
Do you regret any of those intimate experiences with that person? Have you ever had the feeling you were being watched, in general, not during, you know.
What would you do to leave an impression on a person on your first date?
Is there an age where being a virgin, you think, would be awkward?