Cut the bacon in half and stretch it using your fingers. Make sure the dates are pitted. Roll the dates in the bacon starting with the lean end of the bacon and ending with the fat end.
Hold the bacon on with a toothpick. Place on a sheet pan lined with parchment paper. Bake in the oven on a cooling rack. Cook open end down first for about 10 minutes.
Rotate and cook 10 minutes. Rotate again and cook 10 minutes. (They should cook about 30 minutes total).