Without trying to be immodest, I am an attractive woman who is also a bartender, so I have heard every kind of compliment/come-on/verbal leer imaginable…
And I can say honestly that there are lots of ways to pay a woman a compliment without sounding like you have a goal, or intent, other than giving her a sincere compliment.
It’s all in the delivery.
Healthy eye-contact and a warm smile, followed by a short and simple compliment, are never unwelcome. (At least to me. And I’ve heard them all and have a healthy cynicism.)
“You are a beautiful woman,” or “You are such a pretty girl!” etc., etc., are things that could be said any number of ways…but if said respectfully and without leering, they are a charming and welcome compliment and I don’t know many women who wouldn’t like to hear them. I don’t care how young or old the guy is. Equally nice are things like “You have such gorgeous eyes!” or “You have a lovely smile!”
Having said that, it’s different if you approach someone randomly on the street, vs. your bartender or barista or waitress or clerk or whatever…the latter are expected to engage with you to some extent, whereas the former are just walking past you.
But I can recall several occasions in which an older gentleman has passed me on the street, and given me a nod and a big smile, and I assumed that he was paying me a silent compliment.
Even if I’m wrong and he wasn’t, I am of the opinion that other peoples’ approval, whether it’s of your physical appearance, or your intelligence, or anything else, for that matter, is a pleasant feeling. And I don’t see any reason why people–male or female–shouldn’t express it if they feel like it.
I’ve told random women on the street that they have fabulous hair, or great shoes, or gorgeous skin…I’ve complimented strange guys on similar things…
I dunno. I think that we all THINK nice things about other people, and most of the time we don’t say them–myself included–and you never know how it could make someone’s day if you say it out loud. Some of the most welcome compliments I’ve ever gotten were from random people in line behind me at the grocery store. It makes you feel good. Why shouldn’t you pass it on?