In a large pot, heat 2 tablespoons of olive oil over medium heat. Add 1 chopped onion and 2 minced garlic cloves, cooking until the onion is soft and translucent, about 5 minutes.

Stir in 4 cups of canned tomatoes and 2 cups of vegetable broth. Bring to a boil for about 5-7 minutes.

Add 1 teaspoon of salt and 1 teaspoon of pepper, reduce heat to low, and let the soup simmer for 15 minutes.

Blend the soup to your desired consistency using an immersion blender or a traditional blender.

As the soup simmers, prepare the grilled cheese sandwiches with 1 cup of cheese between 2 slices of bread and toast in a pan for 3-4 minutes on each side.

Ladle the soup into bowls and serve with the crispy grilled cheese sandwiches.