Start the tomato soup....
0 Preheat your oven to 400 degrees
2 Place the halved tomatoes, onions and garlic bulb (cut side up) on a large baking sheet
3 Drizzle 1/4 cup of olive oil over everything, toss to coat and season generously with salt and black pepper
4 Sprinkle 2 tablespoons of brown sugar over the onions and add the fresh thyme and oregano
5 Roast the tomatoes, onions and garlic for 45 minutes
Make the grilled cheese...
7 Place a large skillet over medium heat
8 Spread a tablespoon of mayonnaise over one side of each slice of bread
9 Place one slice, mayonnaise side down onto the skillet and top with 2 slices of cheese and 2 ounces of shredded cheese
10 Add the other slice of bread, mayonnaise side up
11 Cook until the underside of the sandwich is crisp and golden brown and then carefully flip the sandwich and cook until the other side is golden brown and the cheese is fully melted
Finish the soup...
13 Remove the thyme and oregano and transfer the roasted tomatoes and caramelized onions into a blender
14 Squeeze the roasted garlic cloves out of the bulb and place them in the blender
15 Add 2 tablespoons of butter, 1/4 cup of heavy cream, 2 cups of vegetable stock, some fresh basil leaves, a pinch of red pepper flakes, a pinch of salt and 1/2 cup of finely shredded parmesan into the blender
16 Blend until smooth, adding additional stock to thin if necessary
Assemble & enjoy...
18 Pour the soup into bowls and top with fresh herbs and more parmesan
19 Enjoy with your grilled cheese… dunking is highly recommended.
