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When you and your friends/homies have some serious facts that could possibly end someone's social life, you have "dirt." "Digging up dirt" simply means you are sharing that "dirt" with others.
"Digging up dirt" means sharing juicy information with others. EX: "Y'all, grab ya shovels I got some serious dirt."

"Oh snap, we're about to dig up some dirt"
by Sierrahmist July 18, 2016
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