weeping willy Share definition Flag Term used to decsribe a penis infected with the clap. See also drippy dick. Paul's careless fornication with the shady ladies at Scroggy's got him a case of the weeping willy. weeping willy by Whiskey Drinker Me January 4, 2010 0 0 Get merch Get the weeping willy mug. Buy Now — $32.95 See more merch