Easy, Main courses, Technique

Bubbe Shirley’s Grilled Cheese and Tomato Sandwiches: A Pictorial Journey

Grilled Cheese and Tomato Sandwich

We would eat these grilled cheese sandwiches three times a day and never tire of them. That’s how good they are. I learned the secret from a friend’s Bubbe. Bubbes know everything. And is there anything better than melted cheese?

Ingredients for grilled cheese and tomato sandwich

Bubbe Shirley’s Grilled Cheese and Tomato Sandwiches

Yield: 3 sandwiches


  • 6 slices of bread
  • Salted Butter
  • Crushed red pepper
  • 3 cheese slices
  • 1 tomato, cored and sliced into 1/8 inch thin rounds


Lay six slices of bread on a bread board as for three sandwiches, but with the outsides facing up—the opposite of how you normally lay the bread for a sandwich—the rounded tops of the slices will be facing each other on the board.

Place generous slivers of butter on the bread slices. You don’t have to worry about covering the whole thing. The butter will melt and spread to cover the bread slices, as the sandwiches cook.

Lay the bottom slices of the sandwiches in a cold skillet, butter side down.

Sprinkle with a very small amount of crushed red pepper.

Sprinkle sparingly with crushed red pepper

Layer tomato slices over bread.

Place cheese slices over tomato layers, folding cheese to fit the bread slices.

Place top layer of bread slices over cheese, butter side up.

Cover skillet with a lid. Place over high heat for 2-3 minutes, or until butter appears to be melting around the edges.

Turn sandwiches. Cook one minute on second side with lid off.

Turn off heat. Cover sandwiches and leave for one more minute to finish melting the cheese

Cut sandwiches in half and serve hot!

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