Preheat your oven to 200°C (390°F) and line a baking sheet with parchment paper or a silicone mat for easy cleanup.
Arrange your pitted Medjool dates on a cutting board and, if using almonds, gently stuff one into the center of each date, pressing softly to hide it inside.
Cut each slice of bacon in half or thirds, depending on the size of your dates, to ensure they are fully wrapped.
Wrap each date snugly with a piece of bacon, securing the end with a toothpick to hold it in place.
Place the wrapped dates evenly on the prepared baking sheet, spacing them apart for proper crisping.
Sprinkle a tiny bit of brown sugar over each bacon-wrapped date for an extra caramelized glaze, and add a pinch of black pepper for a subtle kick.
Bake in the preheated oven for about 15-20 minutes, turning the tray halfway through, until the bacon is golden and crispy, and the dates look caramelized and glossy.
Once cooked, transfer the dates to a wire rack to drain excess fat and let them cool for about 5 minutes—this helps the bacon crisp up further and makes handling easier.
Carefully remove the toothpicks from each date, being gentle to keep the bacon intact.
Serve the bacon wrapped dates warm or at room temperature, enjoying the crispy, caramelized exterior with the tender, sweet interior.
