Preheat oven to 375°F and set the oven rack to middle position. Line a rimmed baking sheet with foil and spray the foil with nonstick cooking spray.
Open the dates lengthwise where they have been opened to remove the pits. If a date isn’t easy to open, slice it lengthwise but not all the way through.
18 fresh Medjool dates
With a small spoon, partially fill the cavity of both sides of the date with goat cheese.
4 ounces goat cheese
For each date, place a pecan half in the middle of one side and press the sides together to close the date.
18 raw pecan halves
Wrap each date with half a slice of bacon (see note) and secure it with a toothpick.
9 slices bacon
Holding the toothpick, dip each prepared date in brown sugar and press the brown sugar all around the date.
¼ cup dark brown sugar
Place the date on the prepared baking sheet and repeat until all dates have been filled.
Bake the dates at 375°F for 10 minutes. Remove from the oven and turn the dates over. Bake an additional 8 minutes. To caramelize the brown sugar on the dates, set the oven to broil and broil the dates about 1 minute per side. Watch the dates closely once the dates are under the broiler.
Remove the pan to a cooling rack and set the dates on a plate to cool to touch.
The dates can be served as is or, if a smaller bite is desired, cut each date into 3-4 slices and serve as “pinwheels”.