Preheat the oven to 400°F (200°C). Line a rimmed baking sheet with aluminum foil for easy cleanup and place a wire rack on top of the sheet. Lightly oil the rack or spray with cooking spray to prevent sticking.

2. Prepare dates

If your dates are not already pitted, make a lengthwise slit in each date and remove the pit. Keep the dates whole otherwise.

3. Fill dates

Using a small spoon or a piping bag, fill each pitted date with about 1/2 teaspoon of goat cheese or cream cheese. If using nuts, press one almond or pecan half into the cheese in each date so it sits snugly inside the cavity.

4. Cut and wrap bacon

Cut each bacon slice in half crosswise to make 24 shorter strips. Take one filled date and wrap one bacon half around it so the ends slightly overlap. Secure the bacon with a toothpick pushed through the top into the date, leaving the toothpick length visible for removal or serving.

5. Optional sugar coating

If using brown sugar, lightly sprinkle or roll the bacon seam side into the brown sugar so a thin coating adheres (this helps caramelize and gives a sweet crust).

6. Season

Lightly season the exposed bacon with a pinch of freshly ground black pepper and a very light dusting of smoked paprika if desired for color and smoky flavor.

7. Bake

Arrange the bacon-wrapped dates on the prepared wire rack seam-side down so they stay wrapped. Bake in the preheated oven for 18–22 minutes, rotating the pan halfway through, until the bacon is crisp and browned to your liking. If bacon is not crisping sufficiently, broil on high for 1–2 minutes while watching closely to avoid burning.

8. Rest and serve

Remove from the oven and let the dates rest on the rack for 3–5 minutes to firm up (they will be very hot inside). Transfer to a serving platter. If you used toothpicks, you can leave them in for serving or remove them before plating. Serve warm or at room temperature.

9. Make-ahead and reheating

These can be assembled a few hours ahead, refrigerated covered, and baked just before serving. To reheat already-baked dates, arrange on a baking sheet and warm in a 350°F (175°C) oven for 6–8 minutes until heated through and bacon re-crisped.

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