Preheat your oven to 375°F (190°C).
In a medium bowl, mix the softened cream cheese, grated Parmesan, chopped spinach, minced garlic, half of the salt, and half of the pepper until well combined. This is your savory filling.
Lay each pork chop flat on a cutting board. Use a sharp paring knife to cut a horizontal pocket into the side of the meat. Cut as deep as you can, being very careful not to pierce through the other sides!
Spoon the spinach and cheese mixture evenly into the pockets of the pork chops. Use toothpicks to seal the openings shut so the cheese doesn't melt out during cooking.
Pat the outside of the stuffed chops completely dry. Season both sides with the remaining salt, black pepper, and paprika.
Heat the olive oil in an oven-safe skillet (like cast iron) over medium-high heat. Sear the stuffed chops for 4 minutes per side to develop a beautiful golden crust.
Transfer the entire skillet to the preheated oven. Bake for 15-20 minutes, or until the internal temperature of the pork reads 145°F (63°C).
Remove the toothpicks, let the meat rest for 5 minutes to lock in the juices, and serve!