Being female and American, I find it a bit easier to compliment people and their watch and clothing choices than my British male friends, but I agree with time and place. Like pick-up lines; how, when, where are important. Expensive watch, late night, on a bus? Keep it to yourself. I tend to be wary complimenting men's watches as well because there is definitely a tendency for the guy to assume I am hitting on him/gold-digging.
And I have seen loads of hilariously bad and amazingly good non-Rolex fakes...
Some of the really bad:
Breitling Bentley Mulliner Tourbillon: hilariously bad, obviously stainless steel with plexi and solid case back.
Breitling Navitimer meets Bentley with an iridescent purple dial, once again with plexi.
Tag Carrera with obviously cracked plastic bezel, plexi and really awful bracelet.
Makes me wish I had pictures.
My favourite is when they stick the fake in my face and ask me what I think.