Adapted from Cook’s Illustrated, New Best Recipes
Makes 5 ½ cups

2 (28 ounce) cans whole tomatoes (not packed in puree), drained, 3 cups juice reserved, tomatoes seeded
1 1/2 Tablespoons dark brown sugar
4 tablespoons unsalted butter
4 large shallots, minced
1 Tablespoon tomato paste
2 Tablespoon all-purpose flour
1 3/4 cups chicken stock
1/2 cup heavy cream
2 Tablespoons brandy
Cayenne Pepper
(Note: the recipe also calls for a pinch of allspice to be added to shallots but I prefer it without)

Adjust oven rack to upper-middle position and preheat oven to 450 degrees; line jelly-roll pan or rimmed cookie sheet with foil.
Pour the tomatoes into a colander over a bowl. Let all the juices drain into the bowl. Carefully open each tomato and remove seeds with fingers. Reserve 3 cups of juice.
Spread tomatoes in single layer on foil, and sprinkle evenly with brown sugar.
Bake until all liquid has evaporated and tomatoes begin to color, about 30 minutes. Let tomatoes cool slightly, then peel them off foil; transfer to small bowl and set aside.
Heat butter over medium heat in dutch oven or medium non-reactive saucepan until foaming; add shallots and tomato paste.
Reduce heat to low, cover, and cook, stirring occasionally, until shallots are softened, 7 to 10 minutes. Add flour and cook, stirring constantly, until thoroughly combined, about 30 seconds.
Whisking constantly, gradually add chicken stock; stir in reserved tomato juice and roasted tomatoes. Cover, increase heat to medium, and bring to boil, Reduce heat to low and simmer, stirring occasionally to blend flavors, about 10 minutes.
Use an immersion blender or carefully transfer into a blender to puree the soup.

Add cream, and heat over low heat until hot, about 3 minutes. Off heat, stir in brandy; season to taste with salt and cayenne, and serve immediately.

To make the heart, mix more cream with the soup in a separate bowl and carefully spoon onto soup in a shape of a heart. Use a toothpick to fix edges.
Also if you are planning on freezing or refrigerating, go ahead, but do not add the cream or brandy. The soup can be refrigerated for 3 days or frozen up to 2 months. Reheat over low heat before proceeding to add the cream and brandy.