Preheat oven at 375 degrees, prepare a sheet pan lined with parchment paper
Slice the dates lengthwise on one side to create an opening. Remove the pit. Using a spoon, stuff a small amount of goat cheese into the cavity of each date and press the sides together to close.
Crack fresh pepper over the dates.
Cut the bacon slices in half. Wrap each date with a slice of bacon and secure with a toothpick.
Arrange evenly on a baking sheet with raised edges (otherwise grease will get everywhere) and bake for 10 minutes. Remove the dates and use the toothpick to turn each one so it’s laying on its side. Bake for another 5-8 minutes, until browned to your liking, and turn the dates to the other side and repeat. For a thicker bacon, bake longer. Remove from the oven, place on a paper towel lined plate, and let stand for 5 minutes before serving.
Having issues with cooking the bacon? Usually, the bacon pieces wrap around the dates 1.5 times. If it’s wrapping more than twice around the date, trim your bacon slices so they’re a little shorter. If that bacon layer is too thick, it won’t cook.
Let cool on a cookie cooling rack, drizzle any choice of honey or balsamic glaze, sprinkle with flaky sea salt and serve warm.