Preheat the oven to 400°F. Line a sheet tray with a silicone baking mat or parchment paper.
Cut dates in half lengthwise, without separating them, stuff with cheese. Close the dates and wrap tightly with a bacon strip. Seal with a toothpick and place all the dates on the prepared sheet tray, with the bacon seam side down. Transfer to the oven and bake the dates until the bacon on top starts to crisp, about 12 minutes.
Meanwhile, in a small bowl, combine maple syrup and red pepper flakes. Remove dates from oven and drizzle maple syrup over the bacon. Place back in oven for 2-3 minutes tops. Sprinkle with chopped rosemary and flaky salt. Serve immediately. Enjoy!
