Hey man, just randomly saw ur dance vids and looked through your posts - u are an amazing kid, for real. You'll always see sentiment like this, especially from guys in places like reddit "missed opportunity bc I didn't pick up on the other person's interest", and it just doesn't matter that much.
For one thing, loneliness is unfortunately just normal, and your brain wants to point to a specific moment to kind of explain away that shitty part of life. It's actually comforting to me reading that you're at least not blaming someone else, but you're not at fault either.
No matter how attractive or smooth, dating is a total crapshoot for all of us. Granted, there's a scale and it's comparatively easier for some, but I promise you that even they are staying up at night reliving missed opportunities or screw ups. There are countless reasons things don't click, or even if they do why they don't progress. You will not likely ever get a simple answer for why one didn't go as you'd have liked.
Yes, being more risk-taking and aggressive can remove that one excuse of "i should have acted", but it's going to create a whole lot of different reasons things don't work out, and possibly create more reasons which might include "i made this person uncomfortable bc i was too aggressive", n that's shitty on just a human level regardless of dating and sex.
A lot of the times we're left questioning "why didn't I act this way", we're putting other people's values in place of our own. Just bc dating and sex are desirable to you, doesn't mean that the things achieving them would they require you to do are inline with your goals, and that's OK. Especially for you - you are a passionate convicted person, I believe you can probably trust yourself to act right (for the most part - there are ways you can fuck this up for yourself, and if you surround yourself with too much of anything it will shift your values). It's hard to be honest with yourself and be patient, but you'll get what you need over time. You will become the person you want to be.
Let me know if you ever want to chat bud. I'll probably delete this soon.