I feel like I need to know everything about the way the world works before I start feeling confident. I feel like this is why I can't be confident. I don't know enough. Is there a theory on this?

For dating think of it more like riding a bike. You can read all the books you want about riding a bike but even knowing everything there is to know about riding a bike, if you've never rid one you won't be able to just hop on a bike able to ride because you don't have actual experience. It's actually riding the bike that gives you that I know how to ride a bike feeling otherwise your just afraid of riding a bike because you are not confident and reading about it is just an excuse for yourself to justify not hopping on the bike until you know everything about bikes.

True confidence is something that comes from within and it's not based on anything external.

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No, true confidence comes only from experience. It comes from DOING. The kind of "knowing" that gives you confidence is from hands-on doing.

Just reading about shit isn't going to give you any confidence. No matter how much you read about driving, the mechanics of how a car works, techniques on the safest race car driving practices, you will never be confident in driving until you've driven a bit. You will NEVER be confident about driving the first time you sit behind the wheel. You just have to buck up and power through the awkward first experiences.

Same goes with pickup. You have to power through those awkward first approaches before getting confident. There is no substitute for real experience.