Daddy Dale Share definition Flag The greatest high school assistant principal in history. Known for his strict enforcement of dress code policies, specifically shaving. "Yo dude, what happened to your beard?" "Daddy Dale sent me to the office to shave" Daddy Dale by ILoveMidway May 14, 2016 0 0 Get merch Get the Daddy Dale mug. Buy Now — $32.95 See more merch