Cook bacon in a large skillet over medium heat until crisp. Remove bacon from skillet and place on paper towels to drain. Leave bacon fat in skillet.
Add apple, onion, and celery to bacon fat and sauté over medium heat until apple mixture softens, about 5 minutes. Add parsley, rubbed sage, 1/2 teaspoon salt, and 1/4 teaspoon pepper. Remove from heat and let cool slightly.
Add stuffing mix, chicken broth, and cheddar cheese to apple mixture and stir until everything is well mixed and chicken broth is absorbed.
Cut a horizontal pocket in the side of each pork chop. Season outside of chops and inside pocket with remaining salt and pepper. Stuff apple mixture into pockets. (Secure with wooden picks if desired. I did not do this.)
Preheat oven to 350 degrees.
Heat olive oil in a large, oven proof skillet over medium-high heat.(If skillet is not big enough to hold all 4 chops, work in 2 batches.)
Add pork chops to pan, handling them carefully so stuffing does not spill out. Saute until lightly browned on each side, about 2 minutes.
Place pan in oven and bake for 15 minutes, or until thickest part of pork chop registers 145 degrees. Remove from oven, cover with foil, and let rest 10 minutes before serving.