Place a 10-inch cast-iron skillet in the wood fired oven for about five minutes to heat up, then remove it. Coat the pan with olive oil.
Place the cheese, dates, dark honey, and the reserved pepper liquid in a food processor and purée until smooth and creamy.
Transfer date mixture to a pastry bag, or a 1-gallon Ziploc bag with a quarter-inch of one corner cut off with a scissors. Pipe the cheese mixture into each Peppadew, just enough to barely fill it. Fill all peppers and set aside.
Slice ham into thirds longways in even strips about 1” wide. Roll one strip of ham around each pepper one way, then turn it 90 degrees, and roll a second piece of ham around each pepper the opposite way. Use only enough ham to roll around each pepper once per turn.
Place each pepper in the oiled skillet with the ham-seam down.
Drizzle the 3 tablespoons of honey over the top of the peppers, then sprinkle on the chopped herbs and black pepper.
Heat your wood fired oven to 650° to 750°F (like when you are cooking pizza.) Place the skillet of peppers in the wood fired oven 6 to 8 inches away from the coals for about 7 to 8 minutes. Baste peppers with juice, then rotate 180° for another 7 to 8 minutes. Rotate the pan again to make sure the peppers are evenly cooked. Continue to baste periodically to keep the peppers moist.
Remove the skillet from the oven and baste again. Let cool for 5 to 10 minutes.
When you are ready to serve, baste the rolled peppers with the pan juices one last time and place them onto the serving plate.