Preheat the oven to 500°. Line a rimmed baking sheet with parchment paper; set aside.
Soak 24 toothpicks in water for 15 minutes. Wrap each date with a piece of bacon, and skewer date with toothpick to hold bacon in place. (Soaking the toothpicks in water prevents them from splintering and burning.)
Place dates seam-sides down on baking sheet.
Bake until tops are well browned, about 6 minutes. Turn, and bake until evenly browned and the bacon is cooked and crisp, 2 to 4 minutes more.
Drain on paper towels. Let cool slightly before serving.