Prep the Chicken: Preheat your oven to 375°F (190°C). Using a sharp knife, carefully slice a pocket into each chicken breast without cutting all the way through.
Prepare Stuffing: In a mixing bowl, combine the shredded cheese, cream cheese, asparagus, minced garlic, salt, and pepper until well mixed.
Stuff the Chicken: Generously fill each chicken breast pocket with the cheese and asparagus mixture. Secure with toothpicks if necessary.
Cook the Chicken: Heat a tablespoon of olive oil in a large oven-safe skillet over medium heat. Add the stuffed chicken breasts and sear for about 5 minutes on each side until golden brown.
Bake: Transfer the skillet to the preheated oven and bake for 20-25 minutes, or until the chicken is cooked through and reaches an internal temperature of 165°F (75°C).
Rest and Serve: Allow the chicken to rest for a few minutes before slicing. Garnish with fresh herbs if desired and serve warm!