Line one or two jelly roll pans (any large shallow pan with sides will do) with aluminum foil. (If you want a little less oily product, place a cooling rack in the pan and when assembling the appetizers, place them on the rack.) Set aside until needed.
Cut bacon strips into halves or thirds crosswise (the pieces should be about 3-4 inches long to allow a small overlap when placed around the date). Place on plate and set aside
Place about 2 to 4 Tbsp of smoked paprika on another small plate and set aside.
Cut the Asiago cheese into sticks about 1/4 inch square by 1 inch long. Place on a separate plate and set aside.
Make your assembly line by starting with the box or container of pitted dates, then the Asiago cheese plate, then the bacon with the paprika plate nearby. Then a container of toothpicks to hold the bacon around the dates. And finally, the foil lined baking pans (with or without optional cooling racks.)
Stuff each date with a small stick of Asiago, take one piece of cut bacon and dip one side in the paprika, then wrap it (Paprika side in) around the date. Toothpick in place and put finished roll on baking pan. Continue in this method until all ingredients are used (or you run out of one of the ingredients.)
Bake at 400°F for 6-8 minutes, turn over and bake for 6-8 minutes more. When bacon is brown and crispy, remove from pan to paper towels to drain.