A new video has rightfully lit up the Internet:
Many guys are asking what the big deal is that guys are telling her she's beautiful or to smile or whatever. I presume they consider harassment to be only what happens in the first few minutes of an episode of Law & Order: SVU.
Allow me to clear it up for you bros, since this video apparently wasn't enough.
It's obvious that you're only talking to her because you think she's hot, and that she owes you something because of it. I don't recall this many people feeling chatty when I went to New York City. For the most part, I wasn't subject to pleas to talk or smile. No men blew past me saying, "Damn!" or, "You don't wanna talk?" Certainly, nobody flanked me for several disturbing minutes.
No, this isn't about friendliness. This is desperate and unnerving. I'd call it having no game, but that implies that there's a game to be played, which is part of the problem with your thinking.
Successful communication is a function of time, place and circumstance. Most importantly, it requires two people who want to talk to each other. In this instance, it's prudent to think before you cat-call: "This woman is trying to get somewhere. To do so, she has to navigate a gauntlet of horny and potentially dangerous strangers, of which I am a part. So should I let her know how beautiful she is?"
No. You should not.
Women are subject to harassment and more subtle power plays on a daily basis from men. By and large, they are the ones more likely to be attacked. And worse, a pervasive cultural sentiment is that women deserve any predatory behavior forced upon them. So at least try to understand why they want guys to leave them alone when conducting their business.
It's not about you; it's about the danger you represent. Opening your mouth only reinforces that notion in her mind. The best thing you can do to reassure her is to say nothing. Be polite. Be decent.
If you're still struggling, think about any time a complete stranger came up to you and went off on some tangent. Even if the person was friendly, wasn't it unsettling somehow? Didn't you question what would motivate them to do such a thing? Didn't you wonder what other impulses they might break out?
That's just the tip of the iceberg for women, and you'll likely never fully understand the scope of that fear. But you can take steps to not add to that fear.
Empathy and decency are beautiful traits.