Headlands School Share definition Flag A place where rapists/sexual offenders/teachers gather. Man 1 : Did you go to Headlands school?Man 2 : YesMan 1: Did you get raped?Man 2 : Yeah. Headlands School by Blottie April 12, 2011 0 0 Get merch Get the Headlands School mug. Buy Now — $32.95 See more merch