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Make the soup: In a 3- to 4-quart saucepan, melt butter over medium-high heat, then add onions. Cook, stirring, until onions are tender and beginning to brown at edges, about 5 to 7 minutes.
Add garlic and cook for 1 minute.
Add tomato paste, and cook for 2 to 3 minutes.
Add sherry, if using, and cook for 1 minute, then tomatoes.
Cook the tomatoes, mashing them slightly with your spoon, for 3 minutes, then add broth and seasoning to taste. Bring mixture to a simmer and cover the pot. Cook at a simmer for 15 to 20 minutes.
To finish: Either with an immersion blender in a full-sized blender, blend the hot soup carefully until totally smooth. Taste, adjust seasoning as needed. If you’d like the soup to be creamy, add it a splash at a time, stirring, until you reach your desired level. Finally, you can add sherry vinegar for a little brightness at the end.
To serve: Ladle into bowls or mugs, finish with a little freshly ground black pepper, and surround with grilled cheese “fingers” for dipping.
To make grilled cheese fingers: Spread the outside of two slices of sandwich bread with either softened butter or a thin layer of mayonnaise. Fill with the cheese of your choice. Cook in a skillet until golden brown on both sides. Cut into strips.