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Step 1
Heat oven to 400°F. Line a large baking sheet with parchment paper.
Step 2
Lay the bacon strips side by side on the baking sheet. Cook for about 10 minutes. (Cook time may vary depending on the thickness of your bacon, so keep an eye on it. The idea is for the bacon to be about halfway cooked yet still soft enough to easily wrap around the dates.)
Step 3
While the bacon is precooking, use a paring knife to make a shallow cut lengthwise in the top of each date, careful not to cut all the way through. Remove the pits, then fill each date with a spoonful of cheese, and use your palm to gently squeeze the date so that it is mostly closed.
Step 4
Once the precooked bacon is cool enough to handle, slice the bacon strips in half. Wrap a strip of bacon around each date and secure it closed with a toothpick.
Step 5
Remove the previous sheet of parchment paper (and any leftover grease) from the baking sheet, and layer on a fresh sheet of parchment paper. Arrange the dates evenly on the baking sheet and season with a few twists of black pepper. Bake for 5-7 minutes per side, flipping the dates halfway through until the bacon is cooked and slightly crispy. (Keep a close eye though so that it does not burn.) Transfer baking sheet to a wire rack and sprinkle the dates with a pinch of flaky sea salt.
Step 6
Serve. Serve warm and enjoy!