Preheat the oven to 400°F. Line a rimmed baking sheet with parchment paper.
Cut a slit into the side of each date. Pinch open the slit slightly; remove and discard the pit. Press the date closed.
Wrap each date snugly with a half-strip of bacon. Secure the end of the bacon with a toothpick inserted through the date.
Arrange the dates, generously spaced, in one layer on the prepared baking sheet. Bake for 15 minutes. Flip the dates and bake until the bacon is cooked to your liking, 7 to 10 minutes more. Transfer the dates to a paper towel–lined plate. Let cool to warm or room temperature, then serve.