This is a problem that I have had to deal with. I am very good at connecting with women, and I really want to get to know them, but once I get to know them I fear that trying any kind of advance might throw a damper on what could develop into a friendship. They are put into the "friend zone".
I once had a woman drug me to have sex with me. On one hand I thought all she had to do was ask, but on further reflection that might not have been enough as there were other considerations. She was someone who I was very much attracted to, a woman who fell into the "hell, yes" category. On the other hand, she was a student in a community college class that I was teaching and there is a good chance that my professional ethics could have overruled my lust.
I also believe that I have a touch of autism and an lack of facility with seeing, interpreting, and trusting my own instincts when it comes to deciding when a woman is interested in me making a move. There have been women who have gotten past that, but they have had to take the bull by the horns and not wait for me to make that move. My dating strategy was to hang out with a woman until she finally rips my clothes off.
Here is my story: https://www.nytimes.com/video/opinion/100000007440367/trump-concede-speech.html?action=click&module=Opinion&pgtype=Homepage