My rule on that is I only compliment women who are older than me. 
Seriously, I freely admit I'm a flirt, but when you compliment accomplishments, abilities, and insights you'll get away with it every time.  It's when you start to objectify and physicalize it that you get in trouble. Funny praising flirty=good. Staring creepy flirting=bad. 
Of course, YMMV, I've been told over and over again that I give off a major "harmless" vibe. I can flirt with a woman in front of her husband (and my wife) with impunity. Maybe I'm just very "metro".
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