I think the most important thing in any relationship (not just romantic) is communication and that's sometimes difficult for people. I've always subconsciously masked but even then, I struggled to understand how two people get to meet each other and build that initial dialogue. I found online dating really helpful, which is where I met my wife. We spent a long time just messaging back and forth before meeting up. During that time using dating sites, I'd forced myself to go on dates, hoping that the new experience would allow me to learn and get better, and they did. They were uncomfortable and I felt like I was talking too much. When I met my wife for the first time, it was really easy. I was definitely different to the other men she had dated and we had honest conversations with each other. I explained that I found it difficult to talk to women and sometimes didn't know what to say and she listened and accepted that. We've been happily married for 10 years now and have a family together.
Being honest with people isn't always going to work (not that you shouldn't be honest), it's just that some people find accepting brutal honesty, difficult. I find it difficult to be subtle, I'm practising and can use subtlety in my job, but it's still hard to do. I just accept that some people are going to read my honest responses the wrong way.
Whatever you decide to do, just take it slowly and try to find small parts of the stressful process to enjoy.
I can only say what helped for me. Research facial expressions and body language. You will then have more information about who finds you attractive and who does not. Access some moral courage and risk rejection, if you do not ask you do not get.
Now when you say “especially with ladies,” I can’t really assume what your gender identity / sexual orientation is, so I can’t determine if you are talking about just making friends with women or going on dates with them.
