I give my son advice on women all the time. He chooses whether to take it or not. He's currently in a situation at school in which a woman is giving him the "signals" but he's too shy to act on it. I encourage him to simply chat with her, but he's not ready.

My other son is a player, which doesn't help his brother's confidence at all.

The fact is, each man has to come into his own. No amount of advice will give you the confidence to make the move in the moment. No amount of advice will teach you to read the room.

And please, for the love of all that is holy, do not date a 22 year old as a 40 year old man. I don't care if you're Brad Pitt, that's predatory. Her prefrontal cortex isn't even fully developed. You have to be the adult in the situation and realize you need to find someone your own age.

It seems like you're still trying to get something from women. That never ends well. You need to discover that women are people and simply form connections where possible. You should check out the dating coach https://medium.com/@michaelchief. As a woman I love what he's teaching about dating, and that's not something I can often say about self proclaimed dating coaches.