Why do girls I'm attracted to not see me the way people close to me do?

Hi, I figured I'd write about it anonymously just to get my thoughts out there. I'm sure many people, not even just guys, can relate to this feeling of being tired of the whole "dating game." Let me preface by saying I think there's a lot of issues inherent in US culture esp around it and so I kinda choose not to participate in it. That said, that doesn't mean I haven't asked people out before, it just means I don't put myself on the open market if that makes any sense.

I think it's important for people to be equal in maturity when you're interested in dating, so usually I'll wait to get to know someone a bit and make sure they're someone I can really respect before asking them out. Every time (granted not that high of a number), I've been rejected, and they have no interest in dating me.

I certainly don't blame anyone for not liking me, each person has their own preferences, but I have to confess I'm a bit confused about some aspects. I feel like if two people are at a similar maturity level and one asks to go on a date, just go on it and try it out lol? It's not committal, and it can be as casual as whatever the other party is comfortable with, it doesn't really need to be that deep.

I'm sort of forced to ask myself then what the reality of the situation is, if I see it one way but what actually ends up happening is always another way.

1. Maybe I'm just not that mature, and I'm overcompensating wayyy out of my league. I would probably assume this first (hooray confidence issues) but each time before I tried something I ask some of the people I know (I have a decently large, tight-knit friend group I wouldn't give up for anything) and they've been like "yeah that would be cool, I think you should go for it." Even people who know me less have told me they think I'd be a really good partner (which is kinda an oddity now that I think about it.) Anyways, as much as I always default to bashing myself, I don't really think this first point is the reason why.
2. I'm probably just attracted to people who ALSO aren't interested in playing the game, and I think oftentimes that means they overthink/overemphasize what a first date is, and put way too much weight on it.
3. It could be a combination of the previous stuff, or maybe smth else entirely. For reference I'm in good shape, I like martial arts as a hobby, and I LOVE music and playing piano so I don't think any of the default "make yourself attractive" answers really apply to me, I feel like I live a decently healthy life for my own sake in the first place. I think really I just don't know how to flirt, and the times I do put a bit extra of myself towards someone they just aren't interested.

So, I'm curious. Does this seem like just a luck thing, I haven't tried enough times? Or does it seem like I'm just coping? Maybe I just choose the wrong types of people to be attracted to with my personality in the first place, and we're not a great match, idk. I don't really expect any life-changing responses but I figured I'd write it out somewhere for my own sake. (For those tempted to say "oh it's a confidence issue you said it in point 2", that's something I struggle with personally, but I make real effort (and have had really good progress over the years) not to let get in the way of my relationships. So I really don't think it's a confidence issue, BUT, feel free to correct me if you're still convinced).

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Anyone who's read this far, thanks for taking your time, and regardless of how good or bad your answer is I hope you have a great day, and appreciate your thought and effort.