27, male.

I have always had a fear of rejection from women and as a result I have avoided asking women out, even the ones I know are attracted to me. This has been an ongoing thing my entire life. The only dates/girlfriends/sex I've had have come as a result of the girl pretty much blatantly telling me that there is a 0% chance of rejection. I generate an okay amount of female attention but I can see that her attraction quickly dissipates once it becomes clear that I have no idea what I'm doing, that I'm not confident in myself, and that I don't really 'know' how to make a move with confidence.

I've passed up countless opportunities in my life where I'm like 85% sure that I can takes things to the next level. I could have made some fun and sexy memories by now but instead my sex life is boring and dull. I've notice that eventually she just gets tired of waiting for me to make a move (yay social norms) and either moves on to someone else and/or just stops trying with me in general.

I realize this is entirely my fault and I feel like I can change this if I could understand how, but I just don't know how, or how to be confident about it. For example there are a few girls on my FB/Instagram who I have at least a bit of history of playfully flirting with, but nothing ever going anywhere. Ideally I'd like to have the balls to message them/escalate things/go on a date but I just freeze up. I've been 'out of the game' so long I'm not even sure how things work anymore.

Advice?