Can't Raise the Main Sail Share definition Flag Erectile dysfunction, either permenant or temporay. A nice way of saying "can't get hard" Damn, she so ugly I can't raise the main sail, even after a case! Can't Raise the Main Sail by Wolf89 January 3, 2007 0 0 Get merch Get the Can't Raise the Main Sail mug. Buy Now — $32.95 See more merch