When you're very proud of a joke, but then realize you should be ashamed. A fusion of pride and shame. usually the reaction to a horrible joke involving: genders, feminism, obesity or problems in the world
One person: "I don't know if I should be proud of that or ashamed that I thought of that"
Another person: "You should be very proud-shamed, buddy."
Another person: "You should be very proud-shamed, buddy."
by DazzTheCornerKid December 6, 2016