I've never understood the "you're pretty, let's go out" thing. If you think I'm pretty, that doesn't mean I think you're pretty or that you smell good or have a nice set of arms. Compliments are not legal tender, and my internal response to them from men in the dating pool is usually a cool "Yes. What do you want?" even though externally I convey demure compliance, which is something I'm working on with my therapist.
That's why I like the freebie in-the-street compliments from men. It's the one area of life where as a woman I'm not expected to respond; where the man can expect no payoff. He must mean it because he couldn't possibly think he's going to get anything in return.
This isn't to minimize the experiences of women who find it threatening when strange men yell compliments at them. Like a lot of the fun, harmless ways that men and women find to relate to each other in a civilized society, it's been ruined by a societal acceptance of sexual aggressiveness and immorality. The problem isn't that women are being too sensitive. The problem is that women end up having to watch their back and, by extension, that men are suspect just for being men because the bad ones look just like the good ones.
But I personally find it threatening when strange men are rude, angry and dismissive, and I find it delightful when they yell "Hey pretty white girl" from across a Berkeley street or "All right darling? You look lovely tonight" when running for a Glaswegian bus. I can smile, or I can not acknowledge it, and then I move on. It's considerably less tiring than carrying on a conversation with a date who can't find anything to talk to me about except my appearance.
And if a man wanted to yell at me in a bar that I'm smart, that would be okay, too. It just hasn't happened yet.
And the thing is, it's a hell of a lot better than being negged.
PS. It isn't only men who compulsively make conversation about externals. An older acquaintance--a trad, by the way--told me at my grandmother's funeral that I'm pale. I am pale. I was also wearing a sleeveless but perfectly appropriate blouse and, shockingly, not thinking about how I looked. And yet the cat lady (she is!!) felt the need to comment "You need to get some of this California sun" which was annoying but fine and then insisted "You're just SO pale" which is when I started wondering if she was hinting that I should put my sweater on and cover my shoulders. Either way, it was my grandmother's funeral. Don't be that person.