painted maypole Share definition Flag a very tall girl who wears lots of make up to hide the fact she looks like shit. OMG LOOK AT THAT PAINTED MAYPOLE, ID RATHER SHAG NAT STREET painted maypole by ROSIE O' B May 6, 2009 0 0 Get merch Get the painted maypole mug. Buy Now — $32.95 See more merch