I guess that it comes a point in life where you need to work with somebody and not just do it on your own. Hence therapy, coaching, or whatever you want to call it. This will help you go through your own insecurities, traumas, awkwardness, role play scenarios, do a trial and error with genuine feedback from a person you trust, and with that internal growth you can approach women as a more self aware and emotionally mature person.

Interesting read, cheers!