Tomato soup and grilled cheese is a crave-worthy combination. In this version, the soup gets its richness from olive oil instead of cream and the sandwiches are done panini-style in an old-fashioned waffle iron. The duo is bound to win over kids and grown ups alike.
Add the tomatoes, 1 cup water, salt, several generous grinds of black pepper. Tear the bread into pieces and add it to the soup.Turn up the heat and bring the soup to a boil. Drop the heat until the soup simmers and cook for 9 minutes.
Use an immersion blender or transfer soup to a conventional blender. Add the remaining olive oil and puree until smooth. Taste and add more red pepper flakes, salt, and/or black pepper if desired. If the soup seems too thick, add more water and blend again.
Preheat a waffle iron.
While the waffle iron is heating, assemble the sandwiches: Lay 4 slices of bread on your work surface and cover each one with cheese, dividing it evenly. Top the sandwiches with the remaining bread slices.
Use a pastry brush to lightly coat the inside of the waffle iron with olive oil. Set one sandwich into the waffle iron and bring the top down firmly (it may not close completely). Cook until the bread is browned and the cheese melted. Remove from the waffle iron and repeat with the remaining 3 sandwiches, lightly brushing the waffle iron with olive oil before each one.
Cut the sandwiches in half and serve with warm cups of soup.