At which point, raise the bar, rinse, repeat. And from reading your post, I'm getting this impression that you view yourself like you're some kind of a freak. That is all you need to do. If you see a woman not a "girl" approximately your age, and you have talked to her for minutes and find yourself attracted to her, then ASK for a date. Just so you know, that's how it's taken many times. For example, I don't believe there is any such thing as the "friend zone".
Everyone's there for the same reason, so no one's going to beat around the bush - If they are into you you will know right away, and vice versa.
I have never been intimate with a woman. Stop thinking of women as prizes go get, things a person deserves, etc. There are explanations elsewhere, but it's a simple language that's pretty unambiguous once you can hear and speak it. And I'm a virgin. But yeah, it's tough to phrase it like that, especially since you're risk-averse - I'm the same way when it comes to women.