How to ask people to do things...

I suck at planning things and I suck at like social etiquette. I struggle when it comes to asking someone who I am not already close with, like a casual acquaintance or someone I'm interesting in dating, to do something.

If you plan something out too far in advance, it just seems like you're making it a thing. If you wait until the last minute (which is what I do) then it might seem like you are using that person as a 2nd option or last resort or you are just lonely/bored/desperate.

I just can't navigate these situations. I get stressed when I try to make plans. I worry that people might be bored or disappointed if what I planned turns out to be boring or shitty, so a lot of times I just wait for other people to make plans and invite me to be a part of them.

I just feel like I'm not bringing much to the table these days and it's something I want to work on.