Those flying the douche bag flag are often called assholes or womanizers, and most have trouble running game. Douche bag flaggers wearing pink are flying the flag extra high.
Girl 2: Who?
Girl 1: The guy with the faux hawk, aviators, and popped collar?
Girl 2: I can't tell which dude out of the frat pack you're talking about, but they're all douche bag flaggin'. I mean, if you want to get drunk and sleep with an asshole, be my guest, but you'll wake up full of herps and regret.