Heat your oven's broiler and place oven rack in the middle position. Strain tomatoes, reserving the juices in a small bowl. Spread tomatoes on a baking sheet, drizzle with olive oil and broil until tomatoes are browning; about 8-10 minutes.
In a food processor or blender combine broiled tomatoes, garlic, chili pepper, carrot, milk, reserved tomato juices, and lemon juice. Puree until the mixture is smooth.
Transfer pureed soup to a medium saucepan and bring to a boil over medium heat. Reduce to a simmer and cook for about 5 minutes, until heated through. Stir in salt and pepper.
Serve in bowls and garnish with parsley and additional black pepper. For extra comfort, be sure to serve the soup with a side of grilled cheese!