Prep & Soak Toothpicks: Preheat oven to 400°F (200°C). Line a large rimmed baking sheet with parchment paper or foil, and place a wire cooling rack on top (baking on a rack allows bacon to crisp on all sides). Soak 20 wooden toothpicks in warm water for 15 minutes to prevent charring in the oven.

Pit & Stuff Dates: Using a small paring knife, make a lengthwise slit down one side of each Medjool date without cutting completely through. Gently open the date and remove the pit. Spoon approximately 1 to 1 1/2 teaspoons of softened creamy goat cheese into the center of each date, pressing gently to close.

Wrap in Bacon: Cut the 10 bacon strips in half crosswise to create 20 shorter strips. Wrap each stuffed date snugly with a half-slice of bacon, overlapping the seam on the bottom, and secure tightly with a soaked toothpick.

Bake to Golden Perfection: Arrange wrapped dates seam-side down on the prepared wire rack. Bake at 400°F for 18 to 22 minutes, turning once halfway through with tongs, until the bacon is deeply golden, rendered, and delightfully crispy.

Glaze & Broil: Brush the hot dates generously with warm hot honey. Switch the oven to broil on HIGH for 1 to 2 minutes until the honey glaze bubbles and caramelizes into a glossy mahogany finish (watch carefully to prevent burning!).

Garnish & Serve Warm: Transfer the crispy bacon wrapped dates to a serving platter. Sprinkle with finely minced fresh rosemary, flaky Maldon sea salt, and a crack of black pepper. Serve warm immediately.