Heat the oven to 375°F and line a baking sheet with parchment paper. In a small bowl, stir together the parsley, cilantro, garlic, olive oil, red wine vinegar, oregano, red pepper flakes, and ½ teaspoon salt to make the chimichurri.
Place the ground beef in a mixing bowl. Add ⅓ cup of the chimichurri and mix gently with your hands until just combined. Divide the mixture into eight equal portions and shape each into a small loaf. Place the loaves on the prepared baking sheet.
Bake the meatloafs for 20 to 22 minutes until they reach an internal temperature of 160°F. While they bake, toss the asparagus with the remaining 1 tablespoon olive oil and ¼ teaspoon salt.
Heat a grill pan over medium-high heat. Cook the asparagus for 6 to 8 minutes, turning occasionally, until it is tender and lightly charred in spots.
Spoon the remaining chimichurri over the baked meatloafs and serve with the grilled asparagus on the side.