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Hey Spidey!Disclaimer: I wrote this whole reply before reading your last update but am still going to post it because I think some of it may be helpful. Btw I think you are pretty much handling the situation perfectly. We can always armchair quarterback and try to analyze where things could have been done differently, that is the luxury of hindsight but you are on the right path and no man makes it through this life without mistakes, rejection and learning the hard way when it comes to dating. The good news is that is where the learning gets done, just don’t over think it , you have learned what you needed to up to this point just keep operating outside of your comfort zone and you literally cannot fill
There is an irony to these situations , which in a way is connected to the ironies of “mindfullness” and happiness in general. As has been mentioned, the very act of over-thinking these situations sort of puts you in a disadvantage from the start. I don’t know if this is practical advice but I’ll share at the risk of writing useless or even counter-productive “advice”
I think you should focus inwards. Focus on your strength , find your joys and (flaky as it sounds) situations like this will sort of become “details”. Not in the sense that they are not important but because they will fall into place naturally and simply. Now do not become overly frustrated or take any of the associated negative feelings to heart. The truth of the matter is that any guy , at some point in their life is bound to be rejected , maybe multiple times until we sort of lose the fear of rejection and become comfortable with our bodies and minds. Once that happens the seduction is just automatic , until then it is awkward but that awkward is all part of growing. The very act of taking the risk of rejection is a very courageous move and honestly, no matter what you will be better for it , that I can promise you.
Women are extremely intuitive and very socially aware (much more so than most guys–myself very much included) so they are going to be onto the “you” which we try very hard to hide from the jump ;). But this is a great thing because it means by changing the inner life we will have a revolutionary effect on how we are perceived. In a way I do think you can “fake it until you make it” but there are very definite limitations on how far you can go with it and its probably less painful to work with what you have.
Some people are able to have that vibe early on. I wasn’t one of those people and never thought I would be. You seem to have a lot going for you so if I could, eventually approach these situations with calm and confidence , please believe me when I say you can or will be able to, if not now , then it is only a matter of time and continuing to take risks in order to expand your vault of experiences.
I’m sorry that there is no simple answers but you have a lot to look forward and ANYTHING you do (within reason) is the right thing to do because as long as you are putting yourself out there you will get results either tomorrow or in the near future.
Good luck!