Brush one side of each slice of bread with olive oil.

Sprinkle Italian seasoning on the oiled sides of the bread.

Lay one piece of bread, oiled side down, in a skillet on medium heat.

Sprinkle cheddar cheese evenly over the bread in the skillet.

Add chopped sun-dried tomatoes to the cheese.

Add chopped black olives to the cheese.

Crumble crisp bacon over the cheese, tomatoes, and olives.

Sprinkle remaining Italian seasoning blend over the fillings.

Top with the other slice of bread, oiled side up.

Cook until the bottom slice is golden brown and the cheese begins to melt.

Flip the sandwich carefully.

Continue cooking until the second side is golden brown and the cheese is fully melted and gooey.

Remove from skillet and serve immediately.