Context is everything. Maybe that guy is a “creepster.” Maybe he’s just a lonely schlub. I don’t know. What I do know is that I was taught by my aunt that I should take compliments graciously and I learned from my single mother to take advances with vigilance and I learned from my wife that some women like when you notice that they’re pretty. Trolling is about as meaningful as the effort you put into it, which is zilch. Telling a woman she’s pretty or telling a man he’s handsome is a gateway to sexual violence the same way smoking weed is a gateway to heroin addiction — it’s the person that matters, not the demographic. So maybe rather than making this guy a poster-child for something far more sinister and truly a problem, just leave him to his cigars and bourbon and loneliness.