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Maybe the reason "douchebags" get the girls is because you automatically label any guy who's successful with a girl you're attracted to a douche. I think that at this point if a guy's wearing a popped collar, it probably got popped by accident, so you have to judge by behavior. And yeah, don't hit on women when they're at work unless you've already made a connection with them in another context and know with reasonable certainty that the answer will be yes.
I was about to write something to this effect, but you said it better.
Keywords
Everyone knows you gotta pop your collar if your a pimp
Don't give up. The worthwhile girls don't go for the popped-collar type anyway.