Heat the pan: Warm a large skillet over medium-high heat and add the oil.
Brown the beef: Add the ground beef, breaking it up with a spatula. Season with salt and pepper.
Cook until browned with crispy edges, about 6–8 minutes. Drain excess fat if needed.
Sauté aromatics: Push the beef to one side. Add onion to the open space and cook 2–3 minutes until softened.
Stir in garlic and cook 30 seconds until fragrant.
Add flavor: Mix in chopped pickle, ketchup, mustard, Worcestershire, smoked paprika, and onion powder. Stir to coat the beef evenly. If using tomatoes, fold them in now.
Melt the cheese: Sprinkle cheese over the skillet.
Reduce heat to low, cover for 1–2 minutes, and let it melt.
Finish and serve: Turn off heat. Top with extra pickles and a drizzle of mayonnaise. Serve over shredded lettuce or alongside a simple salad.