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I can remember friends of mine who worked in retail wearing fake wedding rings to fend off advances, because they happened day in and day out, and guys were pushy, and can remember being chatted up every time we went to a club or out anywhere, every single day I worked at a restaurant or in a retail store, and I am not stunning in looks - if this has declined by 90% it is probably at a reasonable level now. You are right those guys didn't think they were creepy, that doesn't mean they weren't.
Online dating has problems, the commodification of people, etc. but you can't compare it to some ideal that didn't exist.
Not picking up on hints is a separate thing - that is with someone you already know, right? Who is being subtle because they also don't know if you are interested. I think you should feel more free to ask someone you know out and they should feel free to accept or decline without thinking you are creepy for asking. That's not creepy.