1-Step 1: Prepare the Dates Start by preparing your Medjool dates for stuffing. Using a small paring knife, make a shallow lengthwise cut along one side of each date just deep enough to open it without cutting completely through. You want to create a pocket rather than splitting the date in half. Gently remove the pit using your fingers or the tip of your knife. Try to keep the date as intact as possible so the opening stays small and the cheese won’t leak out during baking. Set the prepared dates aside on your work surface.

2-Step 2: Stuff with Cheese Take your chosen cheese whether blue cheese crumbles, softened goat cheese, or feta and carefully stuff about 1 teaspoon into each pitted date. Use your fingers or a small spoon to press the cheese firmly into the pocket. If you’re using goat cheese, you might find it helpful to slightly soften it at room temperature first for easier handling. For blue cheese crumbles, pack them in gently but firmly. The goal is to fill each date generously without overstuffing, which can cause messy leaks during baking.

3-Step 3: Prepare the Bacon Wraps Cut each slice of thin bacon in half crosswise, giving you 20 pieces total perfect for wrapping 20 dates. If you prefer extra bacon coverage, you can leave the slices whole and wrap each date with a full slice, though you’ll need more bacon. For best results, consider partially cooking the bacon before wrapping. Heat a skillet over medium heat and cook the bacon strips for 2-3 minutes per side until they just start to brown but remain pliable. This step helps render some fat and ensures the bacon crisps completely in the oven without overcooking the cheese inside.

4-Step 4: Wrap Each Date Take one piece of prepared bacon and wrap it snugly around a stuffed date. Position the bacon so the seam side faces down when placed on the baking sheet this helps keep everything secure during baking. If your bacon isn’t staying in place, you can secure it with a toothpick. Just remember to soak wooden toothpicks in water for 20 minutes before baking to prevent burning, or use metal appetizer picks that can go straight in the oven.

5-Step 5: Season and Arrange Preheat your oven to 375°F and line a baking sheet with parchment paper or aluminum foil for easy cleanup. Arrange the wrapped dates on the prepared sheet, leaving a small gap between each one to allow for even air circulation and browning. Sprinkle freshly ground black pepper over the tops of each wrapped date. Go easy on the seasoning a light dusting is all you need. The bacon and cheese already provide plenty of savory flavor.

6-Step 6: Bake to Golden Perfection Slide the baking sheet into your preheated oven and bake for 15-20 minutes. Halfway through cooking time, use tongs to carefully flip each date over. This ensures the bacon crisps evenly on all sides. Watch closely after the 15-minute mark. You’re looking for bacon that’s golden brown and crispy, not burnt. The dates should be tender and slightly caramelized, and the cheese should be melted but not oozing everywhere.

7-Step 7: Finish and Serve Remove the baking sheet from the oven and transfer the dates to a serving platter. Sprinkle with flaky sea salt while they’re still hot this helps the salt adhere and adds a wonderful finishing touch of flavor and texture. Let the bacon wrapped dates cool for about 5 minutes before serving. They’ll be extremely hot straight from the oven, and this brief rest also helps the cheese set slightly so it doesn’t ooze out when people take that first bite. If you used toothpicks, consider leaving them in for easy handling at parties.