hey sailor Share definition Flag Hey Sailor is a gay catcall indicating the caller is prowling for quick gay street sex. Boys, just wear assless chaps down Castro Street yelling "HEY SAILOR" and the hunks will come to you! hey sailor by I, Wreckerrr October 14, 2016 0 0 Get merch Get the hey sailor mug. Buy Now — $32.95 See more merch