Directions

• Prepare the Tomato Soup
  Start by preheating your oven to 425°F (220°C). Spread whole tomatoes (preferably vine-ripened) onto a sheet tray. Quarter a yellow onion and scatter it across the tray. Smash a single garlic clove and add it to the mix. Drizzle with olive oil and season generously with salt and freshly cracked black pepper. Roast the vegetables in the oven for about 30-40 minutes until they are soft and slightly caramelized.
• Blend the Soup
  Once the tomatoes, onion, and garlic have roasted, remove the tray from the oven. Let the ingredients cool slightly before transferring them to a blender. Remove any tomato vines and scrape up any caramelized bits from the tray, adding them to the blender. Begin blending on low, then gradually increase the speed. If the soup seems too thick, add a small amount of boiling water to adjust the consistency. After blending, stir in a splash of cream and season with additional salt and pepper to taste.
• Prepare the Grilled Cheese
  While the soup is blending, start working on the grilled cheese. First, grate your cheeses: cheddar, gouda, and fontina, all of which should be finely shredded for easy melting. Combine the cheese in a bowl and mix gently to ensure an even blend. Slice your sourdough bread into thick, even slices.
• Butter and Mayonnaise the Bread
  Spread softened butter evenly on one side of each slice of bread. Next, spread a thin layer of mayonnaise over the buttered side. This combination will give the grilled cheese a perfectly crispy, golden crust. If desired, sprinkle a bit of grated parmesan cheese on the mayo-buttered side for an added layer of flavor and texture.
• Assemble and Grill the Sandwich
  Place a generous amount of the cheese mixture on one slice of bread, ensuring it is evenly distributed. Press the two slices of bread together to form your sandwich. Heat a skillet over medium heat and add a small amount of butter. Place the sandwich in the pan and press gently with a spatula to ensure even contact with the surface. Cook for about 3-4 minutes, then flip the sandwich once the first side is golden brown.
• Finish the Grilled Cheese
  After flipping the sandwich, lower the heat slightly and cover the pan with a lid. This will help the cheese melt completely without burning the bread. Check the sandwich occasionally and adjust the heat as needed. Once both sides are golden and the cheese is melted, remove from the pan.
• Serve
  Serve the grilled cheese with a bowl of your creamy tomato soup. For a decorative touch, drizzle a little olive oil over the soup and add a few fresh parsley leaves. Tear the grilled cheese open and dip into the soup, enjoying the gooey, crispy perfection.