No matter how you cut it, diagonal, crisscross, or tiny bites, grilled cheese and tomato soup are the perfect pairing on a cold, rainy day.
In a large saucepan over medium-high heat, sauté onion in olive oil for 5 minutes; add garlic and sauté another minute. Transfer onion mixture to a blender or food processor, along with tomatoes in juice. Remove crust of 2 pieces of bread and tear in pieces; add to blender and puree until smooth. Transfer soup back to saucepan; add broth, sugar, basil, oregano, and cayenne, salt, and pepper to taste. Bring to a boil over high heat, stirring regularly, then reduce to a simmer; let cook 5 minutes, stirring occasionally.
Meanwhile, heat a large skillet (or an electric skillet if making all 4 at once) to medium-high. Butter bread on the outer facing sides of each sandwich and place the 4 bottom pieces butter-side down in skillet. Top each piece with 2 slices of cheese and place second piece of bread on top, butter-side up. Cover with lid and grill, checking bottom of bread with a spatula after 3 minutes and continuing until bottoms are a medium brown and flip with ease. If cheese isn't fully melted, replace lid while grilling second side. Continue until bread is equally grilled on both sides and cheese is fully melted.
Per serving: 322 calories, 19 grams fat, 8 grams saturated fat, 26 grams total carbohydrates, 37 milligrams cholesterol, 1,131 milligrams sodium, 4 grams fiber, 12 grams protein.
