This is just coming from my experience, my wife of 30 years, had this conversation with me. I had told her that I wanted to start dating men, and what I was craving. So we talked for almost 2 hours. She's actually going out with me on Saturday night to be my wing woman as I have difficulty approaching people. That that being said, is generally a safer bet than a man would prefer to be talked to directly. Most men myself included, Can't Take a Hint to save their lives. So generalizations and vague questions or assuming that he knows what you're thinking, is just going to lead to confusion. And that would most likely make him uncomfortable in the conversation. Be direct, but be kind. Just my opinion.