pop a dingleberry Share definition Flag To cause one to lose their anal virginity. Although the anus technically has no hymen, this is a play on the classic phrase "pop a cherry". "Did you pop a dingleberry?" "Boy, I sure did! Once the ass-hymen broke, shit went everywhere!" pop a dingleberry by sauerkrautbratwurst October 13, 2008 Get the pop a dingleberry mug.