If a juicy cheeseburger and tender meatloaf had a baby, this would be it!
In a skillet over medium heat, warm the olive oil. Add the diced onion and cook until soft, about 4-5 minutes. Then add the minced garlic and cook for 30 seconds until fragrant.
Add the ground beef, breadcrumbs, Parmesan, Italian seasoning, milk, 2 1/2 tablespoons of ketchup, Worcestershire sauce, eggs, salt, pepper, and cheddar cheese cubes to the bowl.
Shape the meat mixture into a loaf on a baking sheet lined with parchment paper. Spread the remaining ketchup on top.