How old is old enough?

A couple days ago, a group of young women (12' ish in age) from our Church came to our house (my wife is an adviser) for a meeting. I was out working in the yard. They all waved and said high to me. I waved back, and was thinking about what exceptional young women they are; Smart, Kind, Modest,... just plain good people.

And then for some reason I had a random thought about how those poor girls are hearing - every time they pick up a magazine, or turn on the TV - about how inadequate they are. That's how a good deal of marketing works after all. I mean, at some point everyone knows about your product, so what is the point of further marketing? To get said people to buy your product (or more of your product). And one proven method for doing that is to convince people that they are somehow incomplete without said product.

So these girls are constantly being told they aren't skinny enough, tall enough, athletic enough, tan enough, pretty enough. Wrong hair, wrong eyes, wrong complexion, wrong shape...

And as I went through this train of thought, I suddenly wanted to be a voice in opposition to that deluge. I wanted to say say something like," how are you lovely ladies doing?".

I didn't.

See, when you are a teenage boy, you can say stuff like that. It is called flirting, it is the natural order of things. Little old men can as well, because they are cute and sweet. They are adorable little grandpas.

But then there is that space in between, when it is creepy. When the girls (and most everyone else) goes quiet, and disengages the safety on their pepper spray. And justifiably so. It seems there is no dearth of creepy at present.

But where does that threshold fall? At what age do you go from creepy to sweet?