Stress!

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I can understand why you wouldn't want to risk repeats of what happened in your 20s, but you were a different person then, those mistakes/experiences are not relevant to the person you are today, but might be feeding into your state of analysis paralysis.
Is your subtle approach with this guy the source of your stress?
Can you be direct and ask him out for a proper date, is that something you are comfortable with? Take the risk that he will say no, and you wont have invested too much time hopefully reducing the foolish feeling/impact on your well being.

I think i feel outside of the whole situation. Maybe like a kind of dissasociative thing. I feel like I am not a part of his life, I can't imagine being a part of his life, therefore I don't know how I could be a part of his life. It seems impossible. It may be possible, but I can't envision it.

I'm not a part of his friend group. I'm on the outside. I don't feel like I'm meant to be here. I feel awkward.

I don't really comprehend the situation.

I think other people would just roll with it and not overthink it. They would see no walls. They'd just see a person they like who seems to like them and just get on with it.

I can't do that for some reason. I feel like an imposter. I've had loads of signals from him, but I keep thinking maybe this isn't real. Maybe I'm reading too much into small things. Or maybe he's just flirting and it's nothing but a little fun for him and i've gone and developed serious feelings. Although he isn't leading me on. He's not deliberately trying to get a reaction out of me.

He is really interesting to talk to. I want to get to know more about him. But I don't want any commitment. I feel like asking for a proper date is too much seriousness. I'm not ready for that. I have time to waste. Nothing else is happening. I'm not going to reject someone else who actually makes a move because of pining after him. Although I find it unlikely that I'll meet anyone else soon, but I won't reject them if I do.

I'm scared, but I don't know what of and I don't know why.

I've been on my own too long. This situation is unusual for me.

I am aware that some of my thoughts are contradictory.

You are over thinking this and it's not healthy.

If you were to ask him out/tell him how you feel/something! then I think it would make you feel a lot better regardless of his response.

The worst that could happen is that he doesn't feel the same way, it's not like he is a complete stranger.

Ask him out for a coffee in the most innocent fashion you can muster, work from there.

Ah I think I understand your perspective better now, though I think life is too short to waste any time .
Do you usually experience this with crush, where you have to know him for a while before you would be interested in commitment? How do you confirm this without dating them?

Long enough that we can converse comfortably.

But I never get that far, so I dunno

Just ask the guy if he would like to grab a coffee sometime.

You are just chasing your tail around yer heid.

^Or a trip to a museum/gallery/craft fair, something with displays to talk about.
Good night Hurtloam, I hope you sleep well.

Here is a story.I'm afraid it's true.

I've lived in a small town for almost 5 years, I still have no friends, sometimes someone in my family takes pity on me and visits. We usually go out for a drink, I never go out socially if no-one drags me out, I try to keep up with them drinkwise, but I'm not used to drinking outside of my room and my pc, all the social stuff just destroys me. Three weeks ago, my very good friend and ex-BIL(he was married to my big sister) visited me in my small town and I tried to match his drinking, as you do, I ended up asking a barmaid out for a coffee. I'm completely mortified at my actions, it's embarrassing firstly, but I also feel bad for asking her out while she was working, just seems wrong. I may never visit that pub again.

I understand how you feel, I still think you should go for it.
Good reason - you felt those first little sparks at church, very dull and boring place, that counts for something.

If you do ask him out and he runs screaming, then you can tell us and we will understand. If he says 'yes, I'd love to grab a coffee with you' then you can tell us and we can cheer you on.
It's really a win-win when you think about it.

Ok, I will do something about this. I won't just pine at a distance

You sound like a very good person. Don't be sad... I hope that you're happy everyday.