what i've derived from my north american anecdata is that any kind of flirtation or even just talking to a stranger about a neutral topic is increasingly automatically graded as creepy. I'd say the social fabric has simply degraded to the point that people have forgotten how to talk to one another, social atrophy i guess. In my northern europe experience women deflect attention with much less fearfulness, and I'd say people just have much higher trust towards one another.

I'm too old, and my kids too young, so the current landscape is foreign to me.

As an outside observer, could it be that manosphere influence has an undue effect on young mens behavior, which (if true) would indeed be creepy for a lot of (most?) women, regardless if the execution is awkward or not.

I was certainly awkward in my teens/young adulthood, but in my singular experience, the maturity and confidence didn't come from acting cocky or showing off, but just treating anyone I had an interest in as a person first and foremost, and being comfortable and even open about my awkwardness and shortcomings.

That did wonders. Also accepting that a rejection doesn't mean a personal slight to you, nor a failure in appreciation of you from her, but merely a lack of mutual interest, which is also fine.