Issues with breaking the ice with prospects

I (27M) have been in the AM market for a year now. During this time, I came across a few matches that I felt could be "the one". But I lost them, due to, I believe not building a rapport.

On paper, everything is good - Earning relatively high, healthy lifestyle, good education, have adventurous hobbies, travel a lot. Thus, I feel the issue is with how I am attempting to break the ice with prospects, also the feedback I receive from a few, indicates the same. And it's not like I do attempts with out-of-my-league prospects or with someone who is from completely different background (religion/caste/community).

My dilemma is, I try playing safe to make them feel comfortable. Start with random small-talk conversations, like, their work, hobbies, food, etc. I want to know about their childhood, their nature, what makes them sad/happy/disappointed/cheerful/etc. (sorry for being dramatic here xD). More often, I don't see the girls to take initiatives to start the conversation, that's a different topic altogether though.

I show genuine curiosity in knowing the person. But what I frequently encountered was, most of them reply after a few hours or next day. Although I don't take it personally, it kills the energy of ongoing conversation for me. Then it suddenly starts feeling like an interview! That leads to eventually nowhere. What can I do here? What can I ask and how can I ask so that it doesn't feel like an interview to the person?

I am okay/accept if you think how a 27M person doesn't know what/how to talk to a girl - But I want to learn. I have been single for the past 5 years, don't have a sister-sibling, none female bestfriends, so I guess this is obvious.

Any suggestions and tips would be appreciated.