A person who's a very obnoxious asshole. An anal flagger is someone who has passed the level of douchebag in their behavior and is headed for asshat status.
Steve: "Everyone hates Todd because he's so rude and obnoxious! He acts like such a douchebag!"
Ryan: "Yeah, Todd's a real anal flagger!"
Ryan: "Yeah, Todd's a real anal flagger!"
by Caryn Rose January 25, 2009