Dude, you're not a terrible person for wanting to be assured that at least some women find you attractive. And from the sounds of it, wanting to be assured that being with your wife is an informed decision, rather than because you think you couldn't get anyone else.

Yes you have had a rough time with your attempts with women. So do a lot of men, but you are more sensitive and respectful than most so feel the rejection more keenly.

I think for most people, being able to meet someone and then be doing something with them within 48 hours or whatever is a fantasy. Possibly it happens more amongst ppl in their late teens/early 20s. But you're not alone in wondering how people actually pull that off (and actually enjoy themselves instead of it beinga kind of crappy experience).

Also, I'm sure you know this already, but Cosplay girls/Instagram/Pinterest are NOT an accurate representation of reality. And for genuine mutual attraction to occur, both people have to be on a similar level in at least a few domains, including so called attractiveness (as in, model looking people tend to get with other model looking people, sporty with sporty, etc). You'll be forever unsatisfied if you're idealising the kind of woman you see on one of those sites.